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Substance Name: Yohimbine hydrochloride [USP:BAN]
RN: 65-19-0
UNII: NB2E1YP49F
InChIKey: PIPZGJSEDRMUAW-VJDCAHTMSA-N

Note

  • A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION. It is also alleged to be an aphrodisiac.

Molecular Formula

  • C21-H26-N2-O3.Cl-H

Molecular Weight

  • 390.908
 

Classification Code

  • Human Data
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Names and Synonyms

Name of Substance

  • Yohimbine hydrochloride [USP:BAN]

Synonyms

  • 17alpha-Hydroxy-20-alpha-yohimban-16-beta-carboxylic acid, methyl ester, hydrochloride
  • AI3-60247
  • Antagonil
  • Aphrodine hydrochloride
  • EINECS 200-600-4
  • NSC 19509
  • UNII-NB2E1YP49F
  • Yohimbe
  • Yohimbin HCl
  • Yohimbin hydrochloride
  • Yohimbin hydrochloride [USP]
  • Yohimbine hydrochloride
  • Yohimbine monohydrochloride

Systematic Names

  • Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester, hydrochloride
  • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, hydrochloride (1:1), (16alpha,17alpha)-
  • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16alpha,17alpha)-
  • Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester, monohydrochloride (8CI)
  • Yohimbine hydrochloride

Registry Numbers

CAS Registry Number

  • 65-19-0

FDA UNII

  • NB2E1YP49F

System Generated Number

  • 0000065190

Molecular Formulas

Molecular Formula

  • C21-H26-N2-O3.Cl-H

Molecular Formula Fragments

  • C21-H26-N2-O3
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C21H26N2O3.ClH/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24;/h2-5,12,15,17-19,22,24H,6-11H2,1H3;1H/t12-,15-,17-,18-,19+;/m0./s1

InChIKey

PIPZGJSEDRMUAW-VJDCAHTMSA-N

Smiles

c12[C@H]3[N@@](C[C@@H]4CC[C@@H]([C@@H]([C@@H]4C3)C(OC)=O)O)CCc1c1ccccc1[nH]2.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo subcutaneous 20mg/kg (20mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC
"Zur Pharmakologie der Yohimbealkaloide, Dissertation," Langer, J., Institute fuer Pharmakologie und Experimentelle Therapie der Universitat Breslau, Poland, 1932Vol. -, Pg. -, 1932.
frog LD50 parenteral 26mg/kg (26mg/kg)   Bulletin des Sciences Pharmacologiques. Vol. 47, Pg. 33, 1940.
frog LD50 subcutaneous 34mg/kg (34mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 137, Pg. 305, 1943.
guinea pig LD50 intraperitoneal 42mg/kg (42mg/kg)   Bulletin des Sciences Pharmacologiques. Vol. 47, Pg. 33, 1940.
man TDLo oral 133ug/kg (0.133mg/kg) BEHAVIORAL: EUPHORIA American Journal of Psychiatry. Vol. 141, Pg. 1267, 1984.
mouse LD50 intraperitoneal 45mg/kg (45mg/kg)   United States Patent Document. Vol. #4179510,
mouse LD50 oral 40mg/kg (40mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Journal of Pharmaceutical Sciences. Vol. 51, Pg. 345, 1962.
mouse LD50 subcutaneous 43900ug/kg (43.9mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
British Journal of Pharmacology and Chemotherapy. Vol. 21, Pg. 51, 1963.
mouse LDLo intravenous 15mg/kg (15mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 50, Pg. 241, 1935.
rabbit LDLo intravenous 5mg/kg (5mg/kg)   "Zur Pharmakologie der Yohimbealkaloide, Dissertation," Langer, J., Institute fuer Pharmakologie und Experimentelle Therapie der Universitat Breslau, Poland, 1932Vol. -, Pg. -, 1932.
rat LD50 intraperitoneal 55mg/kg (55mg/kg) AUTONOMIC NERVOUS SYSTEM: CENTRAL SYMPATHOLYTIC

BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 110, Pg. 20, 1957.
women TDLo oral 400ug/kg (0.4mg/kg) BEHAVIORAL: EUPHORIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
American Journal of Psychiatry. Vol. 141, Pg. 1267, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 289 dec deg C   EXP
log P (octanol-water) 0.750 (none)   EST
Water Solubility 7300 mg/L 20 EXP
Vapor Pressure 1.39E-18 mm Hg 25 EST
Henry's Law Constant 1.83E-24 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.68E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.