(-)-Scopolamine
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(-)-Scopolamine
structure -
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CAS No:
51-34-3
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Formula:
C17H21NO4
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Chemical Name:
(-)-Scopolamine
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Synonyms:
Benzeneacetic acid,α-(hydroxymethyl)-,(1α,2β,4β,5α,7β)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester,(αS)-;1αH,5αH-Tropan-3α-ol,6β,7β-epoxy-,(-)-tropate (ester);Benzeneacetic acid,α-(hydroxymethyl)-,9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester,[7(S)-(1α,2β,4β,5α,7β)]-;3-Oxa-9-azatricyclo[3.3.1.02,4]nonane,benzeneacetic acid deriv.;Scopolamine;Atrochin;Atroquin;(-)-Hyoscine;Hyoscine;9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol (-)-tropate;(-)-Scopolamine;Scopine (-)-tropate;6β,7β-Epoxy-3α-tropanyl S-(-)-tropate;6,7-Epoxytropine tropate;Scopine tropate;SEE;l-Scopolamine;Transderm-Scop;Scop;Scopoderm TTS;Tropic acid ester with scopine;Transcop;97991-84-9;14797-94-5;28901-63-5;58670-87-4;65319-33-7;226562-00-1
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CAS No:
Description
Scopolamine is a high affinity (nM) muscarinic antagonist. 5-HT3 receptor-responses are reversibly inhibited by Scopolamine with an IC50 of 2.09 μM.
LSM-1330 is a 3-hydroxy carboxylic acid.|Scopolamine as a natural plant alkaloid that has potent anticholinergic effects and is used to treat mild to moderate nausea, motion sickness and allergic rhinitis. Scopolamine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.|An alkaloid from SOLANACEAE, especially DATURA and SCOPOLIA. Scopolamine and its quaternary derivatives act as antimuscarinics like ATROPINE, but may have more central nervous system effects. Its many uses include an anesthetic premedication, the treatment of URINARY INCONTINENCE and MOTION SICKNESS, an antispasmodic, and a mydriatic and cycloplegic.
(-)-Scopolamine Basic Attributes
303.35
303.35
200-090-3
DTXSID6023573
Viscous liquid
A - Alimentary tract and metabolism|N - Nervous system|S - Sensory organs
29399990
Characteristics
62.30000
0.76
White crystalline powder
1.3±0.1 g/cm3
55 °C
460.3±45.0 °C at 760 mmHg
232.2℃
1.614
95g/L(15 ºC)
-20°C
7.18X10-9 mm Hg at 25 °C (est)
Oral-Rat LD50 2650 mg/kg; Oral-Mouse LD50: 1275 mg/m3/4 hours
Combustible; Fire breaks down toxic nitrogen oxide fumes
D20 -28° (c = 2.7)
Henry's Law constant = 3.36X10-16 atm-cu m/mol at 25 °C (est)
pKa = 7.75
Crystals. Freely soluble in water, dilute alcohol; slightly soluble in absolute alcohol /Methyl nitrate/|Dihydrate: chisel-shaped prisms from ethanol+water, mp 38-40 °C. Monohydrate: efflorescent crystals, mp 55-57 °C. Anhydrous: long prisms, mp 82-82 °C. Very slightly soluble in water; soluble in alcohol, chlorform, ether, oils /DL-form/|ODORLESS /SCOPOLAMINE HYDROBROMIDE USP/|COLORLESS OR WHITE CRYSTALS OR WHITE GRANULAR POWDER /SCOPOLAMINE HYDROBROMIDE NF/|Hydroxyl radical reaction rate constant = 5.97X10-11 cy cm/molec-sec at 25 °C (est)
Safety Information
UN 1544PSN2 6.1 / PGII
26/27/28
25-45
T+
Warehouse low temperature, ventilated, dry
The commercially available transdermal system of scopolamine should be stored at controlled room temperature between 20 and 25 °C. Scopolamine hydrobromide should be stored in tight, light-resistant containers. Scopolamine hydrobromide injections should be stored in light-resistant, single-dose or multiple-dose containers, preferably of USP Type I glass, at 15 to 30 °C; freezing of the injections should be avoided. Commercially available scopolamine hydrobromide soluble tablets should be stored at controlled room temperature (15 to 30 °C).
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl scopolamine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.|Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: scopolamine hydrobromide is included in antidiarrheal drug products. /Scopolamine hydrobromide/
Department of Health & Human Services/National Institute of Environmental Health Sciences, National Toxicology Program; Teratologic Evaluation of Scopolamine Hydrobromide (CAS NO. 114-49-8) Administered to CD-1 Mice on Gestational Days 6 Through 15, NTP Study No. TER85107 (April 6, 1987 ) available at http://ntp.niehs.nih.gov/index.cfm?objectid=0847FF31-90CC-C685-88B4D7EAC975BD44 as of August 16, 2002|Toxicology & Carcinogenesis Studies of Scopolamine Hydrobromide in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report Series No. 445 (1997) NIH Publication No. 97-3361 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709|Department of Health & Human Services/National Institute of Environmental Health Sciences, National Toxicology Program; Scopolamine Hydrobromide (CAS NO. 114-49-8) Administered to CD Rats on Gestational Days 6 Through 15, NTP Study No. TER85106 (April 6, 1987 ) available at http://ntp.niehs.nih.gov/index.cfm?objectid=0847FF31-90CC-C685-88B4D7EAC975BD44 as of August 16, 2002
|Danger|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 13 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
moderately toxic
Despite widespread use over many decades, neither scopolamine nor methscopolamine have been linked to episodes of liver enzyme elevations or clinically apparent liver injury. Scopolamine is metabolized by the liver, but is usually given in low doses (
Scopolamine should be used with care in patients taking other drugs that are capable of causing CNS effects such as sedatives, tranquilizers, or alcohol. Special attention should be paid to potential interactions with drugs having anticholinergic properties; e.g., other belladonna alkaloids, antihistamines (including meclizine), tricyclic antidepressants, and muscle relaxants.|The absorption of oral medications may be decreased during the concurrent use of scopolamine because of decreased gastric motility and delayed gastric emptying.|Concomitant administration of antimuscarinics and corticosteroids may result in increased intraocular pressure. /Antimuscarinics/Antispasmodics/|Antacids may decrease the extent of absorption of some oral antimuscarinics when these drugs are administered simultaneously. Therefore, oral antimuscarinics should be administered at least 1 hour before antacids. Antimuscarinics may be administered before meals to prolong the effects of postprandial antacid therapy. However, controlled studies have failed to demonstrate a substantial difference in gastric pH when combined antimuscarinic and antacid therapy was compared with antacid therapy alone. /Antimuscarinics/Antispasmodics/|For more Interactions (Complete) data for SCOPOLAMINE (8 total), please visit the HSDB record page.
... Male and female F344/N rats and B6C3F1 mice received scopolamine hydrobromide trihydrate (89% pure) in distilled water by gavage for ... or 2 yr. ... 2 YEAR STUDY IN RATS: Groups of 60 male and 60 female rats were administered 0, 1, 5, or 25 mg scopolamine hydrobromide trihydrate/kg body weight in distilled water by gavage for 104 wk. ... 2 YEAR STUDY IN MICE: Groups of 70 male and 70 female mice were administered 0, 1, 5, or 25 mg scopolamine hydrobromide trihydrate/kg body weight in distilled water by gavage for 104 to 105 wk. ... CONCLUSIONS: Under the conditions of these 2 year gavage studies, there was no evidence of carcinogenic activity of scopolamine hydrobromide trihydrate in male or female F344/N rats or B6C3F1 mice administered l, 5, or 25 mg/kg. /Scopolamine hydrobromide trihydrate/|Scopolamine hydrobromide (SCOP) ... was evaluated for toxic & teratogenic effects in timed-pregnant CD rats. Animals were exposed to scopolamine hydrobromide in water, by gavage on gestational days (gd) 6-15. Cesarean sections were performed on gestational days 20. Prior to initiation of the teratology study, a preliminary study was conducted in order to establish appropriate doses for use in the teratology study. Based on the results of the preliminary study, doses of 0, 10, 100, 450, & 900 mg/kg/day scopolamine hydrobromide were administered in the teratology study. The teratology study was conducted using a two-replicate design, with 12-16 animals assigned to each dose group in each replicate. The second replicate was started (gestational days 0) 19 days after the first replicate. In each replicate, females were weighed & observed during daily treatment for clinical signs of toxicity. At sacrifice on gestational day 20, the gravid uterus of each dam was weighed. Following uterine dissection the number & status of uterine implantation sites was recorded. Each live fetus was weighed, sexed, & examined for external, visceral, & skeletal malformations. A total of 21-28 dams (i.e., confirmed-pregnant females)/treatment group were evaluated in the study. Exposure of timed-pregnant CD rats to scopolamine hydrobromide dissolved in distilled water (0, 10, 100, 450, or 900 mg/kg/day) by gavage on gestational days 6-15 produced the following results: 1.Observed maternal or developmental toxicity at 10 mg/kg/day. 2.At doses > or = 100 mg/kg/day scopolamine hydrobromide, a marginal non-dose-related reduction in fetal body weight, & a marginal non-dose-related incr in the incidence of malformations/litter in the presence of significant dose-related maternal toxicity (reduced maternal body weight & weight gain). 3.At doses > or = 450 mg/kg/day, exposure to scopolamine hydrobromide was associated with a significant incr in the incidence of short ribs. This effect was observed in the presence of significant maternal toxicity. 4.At the doses tested (0, 10, 100, 450, or 900 mg/kg/day scopolamine hydrobromide) there was no separation of maternal toxicity from developmental toxicity. In conclusion, exposure of timed-pregnant CD rats to scopolamine hydrobromide at doses up to 900 mg/kg/day on gestational days 6-15 caused no clear evidence of teratogenic response in gestational days 20 rat fetuses. Marginal evidence of intrauterine growth retardation, & a non-dose-related trend toward an incr in the incidence of malformations was observed only at doses that caused significant maternal toxicity. /Scopolamine hydrobromide/|Scopolamine hydrobromide (SCOP) ... was evaluated for toxic & teratogenic effects in timed pregnant CD-1 mice. Animals were exposed to scopolamine hydrobromide in water, by gavage on gestational days (gd) 6-15 & sacrificed on /gestational day/ 17. Prior to initiation of the teratology study, a preliminary study was conducted in order to establish appropriate doses for use in the teratology study. Based on the results of the preliminary study, doses of 0, 10, 100, 450, or 900 mg/kg/day scopolamine hydrobromide were administered in the teratology study. The teratology study was conducted using a three-replicate design, with 10-17 animals assigned to each dose group in each replicate. In each replicate, females were weighed & observed during daily treatment for clinical signs of toxicity. At sacrifice on /gestational day/ 17, the gravid uterus of each dam was weighed. Following uterine dissection the number & status of uterine implantation sites was recorded. Each live fetus was weighed, sexed, & examined for external, visceral, & skeletal malformations. A total of 23-32 dams (i.e., confirmed-pregnant females)/treatment group were evaluated in the study. Exposure of timed-pregnant CD-1 mice to scopolamine hydrobromide dissolved in distilled water & administered by gavage at doses of 0, 10, 100, 450, or 900 mg/kg/day on /gestational day/ 6-15 produced the following results: 1) A no effect level for maternal & fetal toxicity at doses of 10 & 100 mg/kg/day. 2) Marginal maternal toxicity, observed as slightly reduced maternal body weight & weight gain determined at the 450 & 900 mg/kg/day doses, with corrected maternal body weight significantly reduced at 900 mg/kg/day. 3) A marginal reduction in avg fetal body weight/litter at 450 & 900 mg/kg/day. 4) Congenital malformations & anatomical variations were observed, at low levels, in all groups. There was no relationship seen between their occurrence & the level of treatment & they were seen with equal frequency throughout the groups studied. Because of this, scopolamine had no observable effect on any measure of embryotoxicity at any dose level. In conclusion, scopolamine hydrobromide administered to pregnant CD-1 mice during the period of major organogenesis at doses up to 900 mg/kg/day had no adverse effect on prenatal viability, produced no evidence of teratogenesis, & caused only a marginal reduction in fetal body weight at doses of 450 & 900 mg/kg/day, that also caused marginal maternal toxicity. /Scopolamine hydrobromide/
Scopolamine generally is contraindicated in patients with glaucoma (i.e., angle-closure), pyloric obstruction, or urinary bladder neck obstruction. Scopolamine generally also is contraindicated in patients with tachycardia secondary to cardiac insufficiency or thyrotoxicosis and in those with paralytic ileus. The manufacturer states that scopolamine hydrobromide soluble tablets are contraindicated in patients with prostatic hypertrophy or impaired renal or hepatic function. Scopolamine is contraindicated in patients who are hypersensitive to the drug, to any other belladonna alkaloid, or to any ingredient or component in the formulation or administration system.|Transdermal scopolamine should be used with caution in patients with a history of seizures or psychosis, since the drug potentially can aggravate these conditions.|Scopolamine hydrobromide should be used with extreme caution, if at all, in infants and small children. /Scopolamine hydrobromide/|A transdermal scopolamine patch should not be used in the pediatric population, and with extreme caution in the elderly.|For more Populations at Special Risk (Complete) data for SCOPOLAMINE (7 total), please visit the HSDB record page.
A solanaceous alkaloid derivative from members of the plant genera Erythoxylon, Atropa, Datura, Hyoscyamus, and Scopola. The percent of total alkaloid in the leaves of Datura stramonium is 0.25-0.55%.
The distribution of scopolamine has not been fully characterized. The drug appears to be reversibly bound to plasma proteins. Scopolamine apparently crosses the blood-brain barrier since the drug causes CNS effects. The drug also reportedly crosses the placenta and is distributed into milk..
Drug Information
Scopolamine as a natural plant alkaloid that has potent anticholinergic effects and is used to treat mild to moderate nausea, motion sickness and allergic rhinitis. Scopolamine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.
Gastrointestinal Agents
Adjuvants, Anesthesia; Antiemetics; Muscarinic Antagonists; Mydriatics; Parasympatholytics|Although transdermal scopolamine has been shown to decrease basal acid output and inhibit betazole-, pentagastrin-, and peptone-stimulated gastric acid secretion in healthy individuals, it has not been determined whether transdermal scopolamine is effective in the adjunctive treatment of peptic ulcer disease. /Use is not currently included in the labeling approved by the US FDA/|Transdermal scopolamine has shown minimal antiemetic activity against chemotherapy-induced vomiting. /Use is not currently included in the labeling approved by the US FDA/|Scopolamine hydrobromide is used as a mydriatic and cycloplegic, especially when the patient is sensitive to atropine or when less prolonged cycloplegia is required. The effects of the drug appear more rapidly and have a shorter duration of action than those of atropine. Scopolamine hydrobromide is also used in the management of acute inflammatory conditions (i.e., iridocyclitis) of the iris and uveal tract. /Scopolamine hydrobromide/|For more Therapeutic Uses (Complete) data for SCOPOLAMINE (10 total), please visit the HSDB record page.
The use of scopolamine to produce tranquilization and amnesia in a variety of circumstances, including labor, is declining and of questionable value. Given alone in the presence of pain or severe anxiety, scopolamine may induce outbursts of uncontrolled behavior.|Scopolamine in therapeutic doses normally causes CNS depression manifested as drowsiness, amnesia, fatigue, and dreamless sleep, with a reduction in rapid eye movement (REM) sleep. It also causes euphoria and is therefore subject to some abuse. The depressant and amnesic effects formerly were sought when scopolamine was used as an adjunct to anesthetic agents or for preanesthetic medication. However, in the presence of severe pain, the same doses of scopolamine can occasionally cause excitement, restlessness, hallucinations, or delirium. These excitatory effects resemble those of toxic doses of atropine.|Scopolamine-induced inhibition of salivation occurs within 30 minutes or within 30 minutes to 1 hour and peaks within 1 or 1-2 hours after IM or oral administration, respectively; inhibition of salivation persists for up to 4-6 hours. Following IV administration of a 0.6-mg dose in one study, amnesia occurred within 10 minutes, peaked between 50-80 minutes, and persisted for at least 120 minutes after administration. Following IM administration of a 0.2-mg dose of scopolamine in one study, antiemetic effect occurred within 15-30 minutes and persisted for about 4 hours. Following IM administration of a 0.1- or 0.2-mg dose in another study, mydriasis persisted for up to 8 hours. The transdermal system is designed to provide an antiemetic effect with an onset of about 4 hours and with a duration of up to 72 hours after application.|Small doses of ... scopolamine inhibit the activity of sweat glands innervated by sympathetic cholinergic fibers, and the skin becomes hot and dry. Sweating may be depressed enough to raise the body temperature, but only notably so after large doses or at high environmental temperatures.|For more Drug Warnings (Complete) data for SCOPOLAMINE (21 total), please visit the HSDB record page.
Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)|Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)|Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)|Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)|Drugs that bind to but do not activate CHOLINERGIC RECEPTORS, thereby blocking the actions of ACETYLCHOLINE or cholinergic agonists. (See all compounds classified as Cholinergic Antagonists.)
Scopolamine hydrobromide is rapidly absorbed following IM or subcutaneous injection. The drug is well absorbed from the GI tract, principally from the upper small intestine. Scopolamine also is well absorbed percutaneously. Following topical application behind the ear of a transdermal system, scopolamine is detected in plasma within 4 hours, with peak concentrations occurring within an average of 24 hours. In one study in healthy individuals, mean free and total (free plus conjugated) plasma scopolamine concentrations of 87 and 354 pg/mL, respectively, have been reported within 24 hours following topical application of a single transdermal scopolamine system that delivered approximately 1 mg/72 hours. /Scopolamine hydrobromide/|Following oral administration of a 0.906-mg dose of scopolamine in one individual, a peak concentration of about 2 ng/mL was reached within 1 hour. Although the commercially available transdermal system contains 1.5 mg of scopolamine, the membrane-controlled diffusion system is designed to deliver approximately 1 mg of the drug to systemic circulation at an approximately constant rate over a 72-hour period. An initial priming dose of 0.14 mg of scopolamine is released from the adhesive layer of the system at a controlled, asymptotically declining rate over 6 hours; then, the remainder of the dose is released at an approximate rate of 5 ug/hour for the remaining 66-hour functional lifetime of the system. The manufacturer states that the initial priming dose saturates binding sites on the skin and rapidly brings the plasma concentration to steady-state. In a crossover study comparing urinary excretion rates of scopolamine during multiple 12-hour collection intervals in healthy individuals, there was no difference between the rates of excretion of drug during steady-state (24-72 hours) for constant-rate IV infusion (3.7-6 mcg/hour) and transdermal administration. The transdermal system appeared to deliver the drug to systemic circulation at the same rate as the constant-rate IV infusion; however, relatively long collection intervals (12 hours) make it difficult to interpret the data precisely. During the 12- to 24-hour period of administration and after 72 hours, the rate of excretion of scopolamine was higher with the transdermal system than with the constant-rate IV infusion.|The distribution of scopolamine has not been fully characterized. The drug appears to be reversibly bound to plasma proteins. Scopolamine apparently crosses the blood-brain barrier since the drug causes CNS effects. The drug also reportedly crosses the placenta and is distributed into milk..|Although the metabolic and excretory fate of scopolamine has not been fully determined, the drug is thought to be almost completely metabolized (principally by conjugation) in the liver and excreted in urine. Following oral administration of a single dose of scopolamine in one study, only small amounts of the dose (about 4-5%) were excreted unchanged in urine within 50 hours; urinary clearance of unchanged drug was about 120 mL/minute. In another study, 3.4% or less than 1% of a single dose was excreted unchanged in urine within 72 hours following subcutaneous injection or oral administration of the drug, respectively. Following application of a single transdermal scopolamine system that delivered approximately 1 mg/72 hours in healthy individuals, the urinary excretion rate of free and total (free plus conjugated) scopolamine was about 0.7 and 3.8 ug/hour, respectively. Following removal of the transdermal system of scopolamine, depletion of scopolamine bound to skin receptors at the site of the application of the transdermal system results in a log-linear decrease in plasma scopolamine concentrations. Less than 10% of the total dose is excreted in urine as unchanged drug and its metabolites over 108 hours.
Although the metabolic and excretory fate of scopolamine has not been fully determined, the drug is thought to be almost completely metabolized (principally by conjugation) in the liver and excreted in urine.
Following application of a single transdermal scopolamine system that delivered approximately 1 mg/72 hours, the average elimination half-life of the drug was 9.5 hours.
Although other antimuscarinics have been used in the prevention of motion sickness, it appears that scopolamine is most effective. Scopolamine apparently corrects some central imbalance of acetylcholine and norepinephrine that may occur in patients with motion sickness. It has been suggested that antimuscarinics may block the transmission of cholinergic impulses from the vestibular nuclei to higher centers in the CNS and from the reticular formation to the vomiting center; these effects result in prevention of motion-induced nausea and vomiting.|The sole active agent of Transderm Scoop is scopolamine, a belladonna alkaloid with well known pharmacological properties. It is an anticholinergic agent which acts: i) as a competitive inhibitor at postganglionic muscarinic receptor sites of the parasympathetic nervous system, and ii) on smooth muscles that respond to acetylcholine but lack cholinergic innervation. It has been suggested that scopolamine acts in the central nervous system (CNS) by blocking cholinergic transmission from the vestibular nuclei to higher centers in the CNS and from the reticular formation to the vomiting center.
(1R,2R,4S,5S,7s)-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate (norhyoscine); (1R,2R,4S,5S,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl 2-phenylprop-2-enoate (apohyoscine); (2RS)-3-hydroxy-2-phenylpropanoic acid (DL-tropic acid); hyoscyamine
Emergency and supportive measures: Maintain an open airway and assist ventilation if needed. Treat hyperthermia, coma, rhabdomyolysis, and seizures if they occur. /Anticholinergics/|Specific drugs and antidotes: A small dose of physostigmine .... can be given to patients with severe toxicity (e.g., hyperthermia, severe delirium, or tachycardia). Caution: Physostigmine can cause AV block, asystole, and seizures, especially in patients with tricyclic antidepressant overdose. Neostigmine, a peripherally acting cholinesterase inhibitor, may be useful in treating anticholinergic-induced ileus. /Anticholinergics/|Decontamination: Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. Because of slowed gastrointestinal motility, gut decontamination procedures may be helpful even in late-presenting patients. /Anticholinergics/|Enhanced elimination: Hemodialysis, hemoperfusion, peritoneal dialysis, and repeat-dose charcoal are not effective in removing anticholinergic agents. /Anticholinergics/|For more Antidote and Emergency Treatment (Complete) data for SCOPOLAMINE (7 total), please visit the HSDB record page.
/HUMAN EXPOSURE STUDIES/ Scopolamine-induced deficits in cognitive and motor processes have been widely demonstrated in animals and humans, although the role of acetylcholine in working memory is not as well understood. This study examined the role of acetylcholine neurotransmission in visuospatial short term and working memory using the Groton Maze Learning Test (GMLT). The GMLT is a computerized hidden maze learning test that yields measures of component cognitive processes such as spatial memory, working memory, and visuomotor function, as well as their integration in trial-and-error problem solving. Healthy older adults were administered scopolamine (0.3 mg subcutaneous), the acetlycholinesterase inhibitor donepezil (5 mg oral), scopolamine with donepezil, or placebo. Compared to placebo, low-dose scopolamine led to performance deficits on all measures of the GMLT. The greatest scopolamine-induced deficits were observed in errors reflecting working memory processes (e.g., perseverative errors d=-2.98, and rule-break errors d=-2.49) and these impairments remained robust when statistical models accounted for scopolamine-related slowing in visuomotor speed. Co-administration of donepezil partially ameliorated scopolamine-related impairments and this effect was greatest for measures of working memory than short-term memory. By itself, donepezil was associated with a small improvement in visuomotor function. These results suggest that scopolamine disrupts processes required for rule maintenance and performance monitoring, in combination with visuomotor slowing and sequential location learning.|/SIGNS AND SYMPTOMS/ High doses of scopolamine produce CNS effects (e.g., restlessness, disorientation, irritability, hallucinations) similar to those produced by toxic doses of other antimuscarinics.|/SIGNS AND SYMPTOMS/ Scopolamine toxicity usually arises from adulterated products or ingestion of scopolamine-containing plants, producing classic anticholinergic syndrome. Adults as well as children have developed central anticholinergic syndrome with hallucinations and incontinence after being treated with a single transdermal patch.|/SIGNS AND SYMPTOMS/ When transdermal scopolamine has been used for longer than 3 days, withdrawal of its use has occasionally been followed by dizziness, nausea, vomiting, headache, and disturbance of equilibrium.|For more Human Toxicity Excerpts (Complete) data for SCOPOLAMINE (19 total), please visit the HSDB record page.
Boro Scopol
(-)-Scopolamine Use and Manufacturing
Scopolamine is a tropane alkaloid isolated from Datura metel L., Scopola carniolica Jacq., and other Solanaceae.
cholinergic (ophthalmic).
The transdermal patch contains 12.5 mg of scopolamine.
Ophthalmic: Solution: 0.25% Isopto Hyoscine (with benzalkonium chloride; viscous) (Alcon).|Parenteral: Injection: 0.4 mg/mL Scopolamine Hydrobromide Injection (with parabens), (Abraxis). /Scopolamine hydrobromide/|Oral: Tablets, soluble: 0.4 mg Scopace, (Hope). /Scopolamine hydrobromide/|Topical: Transdermal System: approximately 1 mg/72 hours (1.5 mg/2.5 sq cm) Transderm Scop, (Novartis).
COMPARATIVE STUDIES OF COLORIMETRIC, POLAROGRAPHIC, & GAS CHROMATOGRAPHIC METHODS FOR QUANT DETERMINATION OF SCOPOLAMINE IN PHARMACEUTICAL PREPN. GC WAS FAVORED METHOD WITH CAPACITY TO SOLVE ROUTINE ANALYSIS AS WELL AS DIFFICULT PROBLEMS SUCH AS CONTENT UNIFORMITY.|AUTOMATED PRE-COLUMN DERIVATIZATION SYSTEM & COUPLING OF THIS AUTOANALYZER-TYPE SYSTEM WITH HIGH-PERFORMANCE LIQ CHROMATOGRAPHY IS DISCUSSED. LINEARITY OF SYSTEM FOR HYOSCYAMINE & ERGOTAMINE IS SIGNIFICANT IN CONCN RANGES OF 80-200 NG & 240-720 NG/INJECTION, RESPECTIVELY.|Analyte: scopolamine hydrobromide; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards /scopolamine hydrobromide/|Analyte: scopolamine hydrobromide; matrix: chemical identification; procedure: reaction with chlorine and chloroform; formation of a brownish color /scopolamine hydrobromide/|For more Analytic Laboratory Methods (Complete) data for SCOPOLAMINE (19 total), please visit the HSDB record page.
Analyte: scopolamine; matrix: blood (whole), urine; procedure: high-performance liquid chromatography with ultraviolet detection at 200.5 nm
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Food Contaminant -> NATURALLY_OCCURRING_TOXICANT; -> JECFA Functional Classes
Food Contaminant -> NATURALLY_OCCURRING_TOXICANT;
Computed Properties
Molecular Weight:303.35
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:303.14705815
Monoisotopic Mass:303.14705815
Topological Polar Surface Area:62.3
Heavy Atom Count:22
Complexity:418
Undefined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It is contained in Yunnan Sanfensan extract, and its specific pharmacological effects are not listed separately.
Registered Holders
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FINE CHEMICALS CORP PTY LTD
Active
United States
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BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG
Inactive
United States
Recommended Suppliers of (-)-Scopolamine
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CN
4 YRS
Business licensed Certified factoryManufactory Supplier of Chemical Pesticides,Food Additives,Agrochemicals,Active Pharm Ingredients,Flavors and Fragrances,Chemical Catalyst,Chemical Materials,Chem&Pharm Intermediates,Organic Intermediates,Feed Additive -
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Business licensedTrader Supplier of 13-Dimethyladamantane,1-Bromo-35-dimethyladamantane,perhydroacenaphthylene,4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol,CYCLOBUTANE-1,2-DICARBOXYLIC ACID DIMETHYL ESTER, TRANS -
InquiryUnit Price: $1550-1780 /MT FOBCAS No.: 51-34-3Grade: Food GradeContent: 99%
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Business licensedTrader Supplier of Research chemicals,API,Pharmacuetical Raw PowderInquiryCAS No.: 51-34-3Grade: Industrial GradeContent: 99.99% -
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Business licensedTrader Supplier of Amino acid,intermediatesInquiryCAS No.: 51-34-3Grade: Pharmaceutical GradeContent: 99%
Learn More Other Chemicals
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(-)-SCOPOLAMINE
138-12-5
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(-)-Scopolamine methobromide
155-41-9
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1,1,1,3-TETRAFLUOROACETONE
359-43-3
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Ergosterol Formula
57-87-4
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Atropine sulfate monohydrate Formula
5908-99-6
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(-)-Lobeline hydrochloride Formula
134-63-4
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(-)-Securinine Structure
5610-40-2
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2,4,5-Trimethoxyamphetamine Structure
1083-09-6
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What is Pilocarpine
92-13-7
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What is Benzphetamine hydrochloride
5411-22-3