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Substance Name: Yohimbine
RN: 146-48-5
UNII: 2Y49VWD90Q
InChIKey: BLGXFZZNTVWLAY-SCYLSFHTSA-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.

Molecular Formula

  • C21-H26-N2-O3

Molecular Weight

  • 354.4474
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic alpha-2 Receptor Antagonists
  • Adrenergic alpha-Antagonists
  • Adrenergic Antagonists
  • Autonomic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mydriatics
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Urological Agents
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Names and Synonyms

Name of Substance

  • Yohimbine

MeSH Heading

  • Yohimbine

Synonyms

  • 17-Hydroxyyohimban-16-carboxylic acid methyl ester
  • 4-25-00-01237 (Beilstein Handbook Reference)
  • Aphrodine
  • Aphrosol
  • BRN 0097276
  • CCRIS 9415
  • Corynine
  • EINECS 205-672-0
  • Quebrachin
  • Quebrachine
  • UNII-2Y49VWD90Q
  • Yohimbic acid methyl ester
  • Yohimbin
  • Yohimbine

Systematic Names

  • Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester
  • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-
  • Yohimbine

Registry Numbers

CAS Registry Number

  • 146-48-5

FDA UNII

  • 2Y49VWD90Q

System Generated Number

  • 0000146485

Structure Descriptors

InChI

1S/C21H26N2O3/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/t12-,15-,17-,18-,19+/m0/s1

InChIKey

BLGXFZZNTVWLAY-SCYLSFHTSA-N

Smiles

COC(=O)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3c4c(c5ccccc5[nH]4)CCN3C2)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 643ug/kg/3W-I (0.643mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: EXCITEMENT		 Life Sciences. Vol. 30, Pg. 2033, 1982.
man TDLo oral 694ug/kg/3D-I (0.694mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION British Journal of Psychiatry. Vol. 169, Pg. 384, 1996.
mouse LD50 intraperitoneal 16mg/kg (16mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955.
mouse LD50 oral 43mg/kg (43mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955.
mouse LD50 subcutaneous 37mg/kg (37mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955.
rabbit LDLo intravenous 11mg/kg (11mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1418, 1935.
rabbit LDLo subcutaneous 50mg/kg (50mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1418, 1935.
women TDLo oral 5gm/kg (5000mg/kg) BEHAVIORAL: ATAXIA

PERIPHERAL NERVE AND SENSATION: PARESTHESIS

CARDIAC: CHANGE IN RATE		 Annals of Emergency Medicine. Vol. 14, Pg. 1002, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 241 deg C   EXP
log P (octanol-water) 2.73 (none)   EXP
Water Solubility 277 mg/L 25 EST
Vapor Pressure 1.61E-12 mm Hg 25 EST
Henry's Law Constant 2.90E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.74E-10 cm3/molecule-sec 25 EST

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