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Anabasine

Anabasine structure

Anabasine 

structure
  • CAS No:

    494-52-0

  • Formula:

    C10H14N2

  • Chemical Name:

    Anabasine

  • Synonyms:

    Pyridine,3-(2S)-2-piperidinyl-;Anabasine;Pyridine,3-(2-piperidinyl)-,(S)-;3-(2S)-2-Piperidinylpyridine;Neonicotine;(-)-2-(3′-Pyridyl)piperidine;(-)-Anabasine;Anabasin;(S)-(-)-Anabasine;Neonikotin;(S)-Anabasine;NSC 87504;(2S)-2-(Pyridin-3-yl)piperidine;(S)-3-(Piperidin-2-yl)pyridine;3-[(2S)-2-Piperidyl]pyridine;3-[(2S)-Piperidin-2-yl]pyridine;15973-56-5

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Anabasine is a nicotinic receptor agonist.


(S)-anabasine is the (S)-enantiomer of anabasine.|Anabasine is a nicotine analog that is an alkaloid found in tree tobacco (Nicotiana glauca) and is comprised of a pyridine substituted by a piperidin-2-yl group at position 3. Anabasine has been used as an industrial insecticide and, since it is present in trace amounts in tobacco smoke, its detection in urine can be used as an indicator of exposure to tobacco smoke.|A piperidine botanical insecticide.

Anabasine Basic Attributes

162.23

162.23

82637

207-791-3

LMS11II2LO

87504

DTXSID9041607

C124073

Colorless liquid, darkens on exposure to air

29333990

Characteristics

24.9

1

White fine crystalline powder

1.0455 g/cm3 @ Temp: 20 °C

9 °C

270-272 °C

93°C

1.5430

Miscible in water @ 25 deg C

Refrigerator

0.00662mmHg at 25°C

Intravenous-Mouse LD50: 1.62 mg/kg

Flammable; burning produces toxic nitrogen oxide gas

D20 -83.1°

pKa= 11.0 (conjugate acid)

Safety Information

I

6.1

3140

27/28-51/53-23/24/25

28-36/37-45-61-36/37/39-28A

BV4375000

T

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

DARKENS ON EXPOSURE TO AIR

P201, P202, P210, P260, P264, P270, P280, P281, P308+P313, P309+P311, P370+P378, P403+P235, P405, P501

H227

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.

|Warning|H227: Combustible liquid [Warning Flammable liquids]|P201, P202, P210, P260, P264, P270, P280, P281, P308+P313, P309+P311, P370+P378, P403+P235, P405, and P501

Toxicity

highly toxic

ANABASINE ENHANCED SEDATIVE ACTION OF RESERPINE, APOMORPHINE, & 5-HYDROXYTRYPTOPHAN IN FROGS & INHIBITED SEROTONIN UPTAKE BY HUMAN THROMBOCYTES.

IN ANABASIS APHYLLA L, CHENOPODIACEAE...IN NICOTIANA GLAUCA GRAHAM, SOLANACEAE...|Anabasine is the principal alkaloid of Anabasis aphylla, present at 1-2% in the shoots, and is also found to about 1% in Nicotiana glauca(1).

Anabasine's production and former use as an insecticide(1) may have resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 80(SRC), determined from a log Kow of 0.97(2) and a regression-derived equation(3), suggests that anabasine is expected to have high mobility in soil(SRC). However, anabasine has a pKa of 11.0(4), which indicates that this compound will exist in the protonated form at environmental pH values, and cations adsorb more strongly to soils than neutral molecules. Therefore, the mobility of anabasine is expected to be much lower than predicted(SRC). Volatilization of anabasine from moist soil surfaces will not an important fate process(SRC) as it will exist in the protonated form in the environment and the protonated form will not volatilize(SRC). Anabasine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.6X10-3 mm Hg(SRC), determined from a fragment constant method(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 80(SRC), determined from a log Kow of 0.97(2) and a regression-derived equation(3), indicates that anabasine is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 11.0(4) indicates anabasine will exist entirely in the ionized form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), anabasine, which has an estimated vapor pressure of 6.6X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase anabasine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4 hours(SRC), calculated from its rate constant of 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of anabasine with photochemically-produced hydroxyl radicals has been estimated as 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Anabasine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Data are not available to assess this compound's potential for direct photolysis. Anabasine has a pKa of 11.0(3) indicating that this compound will exist as a cation at environmental pH values(SRC).

An estimated BCF of 3 was calculated for anabasine(SRC), using a log Kow of 0.97(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of anabasine is estimated as 80(SRC), using a measured log Kow of 0.97(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that anabasine is expected to have high mobility in soil. However, the pKa of anabasine is 11.00(4), which indicates that this compound will exist in the protonated form under environmental pH values and cations adsorb more strongly to soil surfaces than neutral molecules (SRC).

Anabasine has a pKa value of 11.0, indicating that this compound will exist in the protonated form under environmental pH conditions; cations do not volatilize from either moist soil or water surfaces. Anabasine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.6X10-3 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to anabasine may occur through inhalation and dermal contact with this compound at workplaces where anabasine is produced or used. (SRC)

Drug Information

EXPTL USE: ANABASINE (2 MG/KG/DAY, IP FOR 10 DAYS) INHIBITED THE INHIBITORY EFFECT OF CONCOMITANTLY ADMIN HYDROCORTISONE ON ADRENAL CORTEX-PITUITARY SYSTEM IN RATS. IT ALSO INHIBITED ASEPTIC INFLAMMATION (FORMALIN INJECTION UNDER THE PLANTAR APONEUROSIS OF THE FOOT) IN RATS; THIS ANTIINFLAMMATORY ACTIVITY APPEARS TO BE DUE TO ACTIVATION OF ADRENAL CORTEX-HYPOTHALAMUS-PITUITARY SYSTEM. IT MAY BE USEFUL TO ACTIVATE THE HORMONAL FUNCTION OF ADRENAL CORTEX-PITUITARY SYSTEM DURING GLUCOCORTICOID THERAPY IN PATIENTS WITH INFLAMMATION.

6. 6= SUPER TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) LESS THAN 5 MG/KG; A TASTE (LESS THAN 7 DROPS) FOR 70 KG PERSON (150 LB).

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

Anabasine is readily absorbed from the skin and from mucous membranes.

IN VITRO METABOLISM OF (-)-METHYLANABASINE BY RAT, RABBIT & GUINEA PIG GAVE (-)-ANABASINE WHICH WAS METABOLIZED TO 1'-N-HYDROXYANABASINE & ANABASINE 1'DELTA-NITRONE. METABOLIC PRODUCTS OF FORTIFIED LUNG MICROSOMAL FRACTIONS WERE SIMILAR.

...ANABASINE AFFECT/S/ THE GANGLION OF THE INSECT CENTRAL NERVOUS SYSTEM, FACILITATING TRANS-SYNAPTIC CONDUCTION AT LOW CONCENTRATIONS AND BLOCKING CONDUCTION AT HIGHER LEVELS.|ANABASINE EXERTED NEUROMUSCULAR BLOCKING EFFECT ON ISOLATED RAT PHRENIC NERVE-DIAPHRAGM WHICH COULD BE PARTIALLY ANTAGONIZED BY NEOSTIGMINE. IT IS A DEPOLARIZING MUSCLE RELAXANT WITH SOME CHARACTERISTICS OF COMPETITIVE MUSCLE RELAXANTS.

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Aggressive airway management may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and treat if necessary... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Nicotine and Related Compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Nicotine and Related Compounds/

SYMPTOMATOLOGY: 1. BURNING SENSATION IN MOUTH & THROAT, SALIVATION, NAUSEA, ABDOMINAL PAIN, VOMITING, DIARRHEA. GI REACTIONS ARE LESS SEVERE BUT DO OCCUR AFTER CUTANEOUS & RESP EXPOSURES. /NICOTINE/|SYMPTOMATOLOGY: 2. SYSTEMIC EFFECTS INCL HEADACHE, SWEATING, DIZZINESS, AUDITORY & VISUAL DISTURBANCES, CONFUSION, WEAKNESS, & INCOORDINATION. 3. AT FIRST RESP...DEEP & RAPID, BLOOD PRESSURE...HIGH...PULSE...SLOW. INTENSE VAGAL STIMULATION MAY CAUSE TRANSIENT CARDIAC STANDSTILL OR PAROXYSMAL ATRIAL FIBRILLATION. PUPILS ARE GENERALLY CONSTRICTED. /NICOTINE/|SYMPTOMATOLOGY: 4. CENTRAL NERVOUS EXCITATION...EVIDENCED BY TREMORS & SOMETIMES BY CLONIC-TONIC CONVULSIONS. 5. AS DEPRESSION DEVELOPS, PUPILS DILATE, BLOOD PRESSURE FALLS AND PULSE BECOMES RAPID & OFTEN IRREGULAR. FAINTNESS, PROSTRATION, CYANOSIS & DYSPNEA PROGRESS TO COLLAPSE. 6. DEATH FROM PARALYSIS OF RESPIRATORY MUSCLES. /NICOTINE/|A 29 YR OLD MAN USED THERAPEUTIC CLYSMA OF TAR FOR RECTAL PROLAPSE. HE EXPERIENCED SHARP GENERAL WEAKNESS, VERTIGO & NAUSEA. WHEN EXAM, HE WAS IN EXTREMELY CRITICAL CONDITION. CARDIOVASCULAR SIGNS WERE DISTURBED & THERE WAS ACROCYANOSIS & LOWERED BODY TEMP; PT WAS STILL CONSCIOUS. 35 MIN AFTER 1ST AID RESP BECAME SEVERLY DEPRESSED & HE BECAME UNCONSCIOUS. THERE WAS MARKED CYANOSIS. URINATION WAS FREQUENT & PAINLESS. ANALYSIS OF URINE & STOMACH CONTENTS DEMONSTRATED ALKALOID ANABASINE. NO SEQUELAE APPEARED ON LATER FOLLOW UP.|Acute & subacute toxicity: increased salivation, vertigo, confusion, disturbed vision & hearing, photophobia, cold extremities, nausea, vomiting, diarrhea, syncope, colonic spasms.

Anabasine

Anabasine Use and Manufacturing

Methods of Manufacturing

Extracted on a large scale in Russia. Industrial extraction processes: Sadykov, Timbekov; J Appl Chem USSR 29: 148 (1956).|Derivation: (1) Extraction from Anabasis aphylla and Nicotiana glauca, (2) synthetic

Uses

Nicotinic receptor agonist

Neo-nicotine is a name given to a synthetic anabasine (the DL isomer) produced and tested in the US by the Department of Agriculture.|ANABASINE WAS FIRST DESCRIBED BY AP OREKHOV IN 1929 IN THE PLANT ANABASIS APHYLLA WHICH GROWS IN LARGE QUANTITIES IN CENTRAL ASIA. FOR USE IN AGRICULTURE A 40% AQUEOUS SOLUTION OF THE SULFATES OF THE TOTAL ALKALOIDS OF ANABASIS IS PUT OUT. THE TOTAL ALKALOIDS CONTAIN 70% OF ANABASINE & 30% OTHER ALKALOIDS. IT IS PRACTICALLY EQUAL TO NICOTINE IN INSECTICIDAL ACTIVITY.|Anabasine...is the principal alkaloid of Anabasis aphylla, present at 1-2% in the shoots, and is also found to about 1% in Nicotiana glauca.

...TWO TECHNIQUES /THIN-LAYER CHROMATOGRAPHY AND PHOSPHORIMETRY/ WERE USED...FOR THE /SEPARATION &/ ANALYSIS OF...ANABASINE IN TOBACCO; JD WINEFORDNER, HA MOYE; ANAL CHIM ACTA 32: 278 (1965).|MASS SPECTRAL FRAGMENTATION ANALYSIS USED TO DETERMINE ANABASINE CONTENT OF VARIOUS PARTS OF NICOTIANA GLAUCA (WOODY MATERIAL, LEAVES & BARK).

Computed Properties

Molecular Weight:162.23
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:162.115698455
Monoisotopic Mass:162.115698455
Topological Polar Surface Area:24.9
Heavy Atom Count:12
Complexity:136
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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