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Home > Encyclopedia > Rescinnamine

Rescinnamine

pharmaceutical raw materials
Rescinnamine structure

Rescinnamine 

structure
  • CAS No:

    24815-24-5

  • Formula:

    C35H42N2O9

  • Chemical Name:

    Rescinnamine

  • Synonyms:

    Yohimban-16-carboxylic acid,11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]oxy]-,methyl ester,(3β,16β,17α,18β,20α)-;Rescinnamine;3β,20α-Yohimban-16β-carboxylic acid,18β-hydroxy-11,17α-dimethoxy-,methyl ester,3,4,5-trimethoxycinnamate (ester);Yohimban-16-carboxylic acid,11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-,methyl ester,(3β,16β,17α,18β,20α)-;Benz[g]indolo[2,3-a]quinolizine,yohimban-16-carboxylic acid deriv.;Methyl trimethoxycinnamoylreserpate;Reserpinine (C35 alkaloid);3,4,5-Trimethoxycinnamoyl methyl reserpate;Anaprel;Scinnamina;Apoterin;Cartric;Cinnaloid;Resealoid;Rescisan;Moderil;Rescinnamin;Reserpinine;Reserpic acid methyl ester 3,4,5-trimethoxycinnamate;O-(3,4,5-Trimethoxy-trans-cinnamoyl) methyl reserpate;Apoterin S;NSC 15628;84-34-4;522-78-1;15676-44-5;15676-43-4;25460-29-1;28821-79-6;412909-15-0

  • Categories:

    Biochemical Engineering  >  Chinese Herbs

Description

white to cream powder


Rescinnamine is an odorless white to cream colored crystalline powder. (NTP, 1992)


Rescinnamine is an odorless white to cream colored crystalline powder. (NTP, 1992)

Rescinnamine Basic Attributes

634.72

634.72

246-471-8

1544

DTXSID3023554

Fine needles from benzene|WHITE, OR PALE BUFF TO CREAM-COLORED CRYSTALLINE POWDER

Characteristics

118

3.5

white to cream powder

1.31g/cm3

238.5 °C

756.8ºC at 760 mmHg

411.5ºC

1.621

Practically insol in water; moderately sol in methanol, benzene, chloroform, and other organic solvents

2-8°C

8.5E-23mmHg at 25°C

D24 -97° (c = 1 in chloroform)

ODORLESS

Insoluble in water.

Amines, Phosphines, and Pyridines

The neat material darkens slowly on exposure to light. In solution this occurs more rapidly. (NTP, 1992).

Safety Information

III

6.1(b)

1544

25-20/21/22

22-45-36

Xn

Stable, but darkens slowly in light. Incompatible with strong oxidizing agents.

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501

H302

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.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

Found in Rauwolfia serpentina Benth, Apocynaceae: Haack et al, Naturwiss 41, 214 (1954)...

Drug Information

ORAL ADMIN...OF LITTLE VALUE IN MGMNT OF SEVERE HYPERTENSION & THAT ASSOCIATED WITH TOXEMIA OF PREGNANCY EXCEPT IN CONJUNCTION WITH THIAZIDE COMPD OR MORE POTENT ANTIHYPERTENSIVE DRUGS... /RAUWOLFIA ALKALOIDS/|ANTIHYPERTENSIVE /SRP: LARGELY REPLACED BY MORE EFFECTIVE THERAPY/|TRANQUILIZER /SRP: LARGELY REPLACED BY MORE EFFECTIVE THERAPY/

PT WITH ALLERGIC DISORDERS MAY SUFFER EXACERBATION OF SYMPTOMS. /RAUWOLFIA ALKALOIDS/|HYPOTENSIVE & SEDATIVE EFFECTS ARE ACCOMPANIED BY BRADYCARDIA, BUT CARDIAC OUTPUT & RENAL PLASMA FLOW ARE NOT MARKEDLY AFFECTED. /RAUWOLFIA ALKALOIDS/|EXCEPT THAT SEDATION & BRADYCARDIA OCCUR LESS FREQUENTLY & IN MILDER FORM WITH RESCINNAMINE, INCIDENCE OF OTHER SIDE EFFECTS SUCH AS WEAKNESS & FATIGUE, NASAL CONGESTION, DIZZINESS, CONFUSION, INCR APPETITE, & WT GAIN IS ABOUT THE SAME AS WITH RESERPINE.|UNLESS DOSAGE IS CAREFULLY ADJUSTED, DRUG MAY INDUCE A PARADOXICAL FORM OF ANXIETY & ADVERSE REACTIVE DEPRESSION. ... SUICIDAL DEPRESSION IS MOST SERIOUS UNTOWARD EFFECT. ...SHOULD BE USED CAUTIOUSLY IN PT WITH HISTORY OF PEPTIC ULCER. ... CONTRAINDICATED IN ECLAMPSIA & IN NURSING MOTHERS... /RESERPINE/|For more Drug Warnings (Complete) data for RESCINNAMINE (11 total), please visit the HSDB record page.

3 & 4. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB).

SEE RAUWOLFIA ALKALOIDS. NEITHER TOELRANCE NOR HABITUATION...REPORTED. /RAUWOLFIA ALKALOIDS/

RAUWOLFIA ALKALOIDS ARE ABSORBED READILY FROM GI TRACT & FROM PARENTERAL SITES OF INJECTION.|SEE RAUWOLFIA ALKALOIDS. ...PASS PLACENTAL BARRIER & MAY AFFECT NEWBORN. /RAUWOLFIA ALKALOIDS/

SEE RAUWOLFIA ALKALOIDS. ...PRODUCE VARIABLE LOWERING OF MEAN ARTERIAL BLOOD PRESSURE...BY BLOCKING AFFERENT IMPULSES WHICH...STIMULATE SYMPATHETIC VASOPRESSOR REFLEXES NEAR LEVEL OF HYPOTHALAMUS &/OR BY DECR REACTIVITY OF PERIPHERAL SYMPATHETIC...SYSTEM THROUGH DEPLETION OF NOREPINEPHRINE @ NERVE ENDINGS. /RAUWOLFIA.../|SEE RAUWOLFIA ALKALOIDS. ALSO EXHIBIT A NON-HYPNOTIC SEDATIVE EFFECT WHICH MAY BE ASSOCIATED WITH THEIR ABILITY TO MODIFY CONCN OF SEROTONIN &/OR NOREPINEPHRINE IN BRAIN STEM. /RAUWOLFIA ALKALOIDS/

SYMPTOMS: Symptoms of exposure to this compound may include dyskinesia, behavioral toxicity and cardiovascular effects. Ingestion may cause depressed activity and it is antipsychotic. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

TREATMENT: 3. EPIGASTRIC PAIN &...PEPTIC ULCER MAY REQUIRE LOCAL ANTACID THERAPY... 4. ...MOTOR DYSFUNCTION...OFTEN CONTROLLED BY DRUGS USEFUL...IN PARKINSONISM, BUT SAFER COURSE IS TO DISCONTINUE RESERPINE THERAPY... /RESERPINE/|TREATMENT: 5. IN ACUTELY POISONED PT...NOT IN COMA, EMESIS...OR GASTRIC LAVAGE...EVEN SEVERAL HR AFTER INGESTION... LEAVE SALINE CATHARTIC IN STOMACH. 6. ...COMA WITH HYPOTENSION...RESPONDS TO CONSERVATIVE SUPPORTIVE THERAPY. ANALEPTIC DRUGS...PROBABLY MORE DANGEROUS THAN BENEFICIAL... /RESERPINE/|TREATMENT: 7. USE BLANKETS &...EXTERNAL...HEAT TO MAINTAIN BODY TEMP... 8. UNLESS BLOOD PRESSURE BECOMES VERY LOW, AVOID VASOPRESSOR DRUGS... MAY LEAD TO EXAGGERATED CARDIOVASCULAR RESPONSE... 9. BECAUSE OF UNCERTAIN CARDIAC STATUS...AVOID RAPID IV INFUSIONS... /RESERPINE/|TREATMENT: 10. ALTHOUGH NOT DESCRIBED IN CLINICAL POISONINGS, RAPID DIGITALIZATION WITH OUABAIN OR ACETYLSTROPHANTHIDIN MAY AID...ADEQUATE CIRCULATION, ALTHOUGH THERE MAY BE HIGH RISK OF CARDIAC ARRHYTHMIAS. /RESERPINE/|SEE RAUWOLFIA ALKALOIDS. A SYMPATHOMIMETIC...SUCH AS METHAMPHETAMINE IS SUGGESTED TREATMENT FOR OVERDOSAGE. /RAUWOLFIA ALKALOIDS/

SEE RAUWOLFIA ALKALOIDS. OVERDOSAGE...CHARACTERIZED BY CENTRAL DEPRESSION...PTOSIS, MIOSIS, & CATATONIA IN SEVERE CASES. /RAUWOLFIA ALKALOIDS/|...USEFUL FOR MANAGEMENT OF MILD, LABILE HYPERTENSION & AS TRANQUILIZING AGENT IN AGITATED PT WITH SIMPLE NEUROSES & FRANK PSYCHOSES.|...ADMIN ORALLY...HAVE CUMULATIVE ACTION; MAX RESPONSE USUALLY NOT OBSERVED UNTIL SEVERAL DAYS TO 2 WK AFTER THERAPY IS INITIATED, & SOME EFFECT MAY PERSIST UP TO 4 WK AFTER THERAPY IS DISCONTINUED. /RAUWOLFIA ALKALOIDS/

Rescinnamine Use and Manufacturing

Methods of Manufacturing

...from Rauwolfia spp: Banes et al, J Am Pharm Assoc 47, 625 (1958).

Uses

Rescinnamine occurs in the roots of a num ber of Rauwolfia species. Therapeutically, itis used as an antihypertensive agent.

A PURIFIED ESTER ALKALOID OF THE ALSEROXYLON FRACTION OF RAUWOLFIA SPECIES.|Found in Rauwolfia serpentina Benth., Apocynaceae: Haack et al., Naturwiss. 41, 214 (1954); Ordway, Guercio, US pat 2,876,228 (1959 to Pfizer); Klohs et al, US pat 2,974,144 (1961 to Riker)...|...AVAILABLE TO THE PHARMACEUTICAL MANUFACTURER IN FORM OF...PURE CRYSTALLINE ALKALOIDS...RESCINNAMINE...|...DIFFERS STRUCTURALLY FROM RESERPINE IN THAT IT IS TRIMETHOXYCINNAMIC ACID ESTER RATHER THAN TRIMETHOXYBENZOIC ACID ESTER OF METHYL RESERPATE. ... PHARMACOLOGIC ACTIONS OF RESCINNAMINE ARE INDISTINGUISHABLE FROM THOSE OF RESERPINE.

AOAC Method 961.2.1 Determination of Rescinnamine in drugs. Spectrophotometric method.|GAS CHROMATOGRAPHY. PARKER ET AL, ANAL CHEM 34, 757 (1962).|THIN-LAYER CHROMATOGRAPHY. ZINGALES, I, J CHROMATOGR 31, 407 (1967).|THIN-LAYER CHROMATOGRAPHY. ZINGALES, I, J CHROMATOGR 31, 407 (1967.|For more Analytic Laboratory Methods (Complete) data for RESCINNAMINE (6 total), please visit the HSDB record page.

Computed Properties

Molecular Weight:634.7
XLogP3:4.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:11
Exact Mass:634.28903092
Monoisotopic Mass:634.28903092
Topological Polar Surface Area:118
Heavy Atom Count:46
Complexity:1080
Undefined Atom Stereocenter Count:6
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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