Skip Navigation
ChemIDplus A TOXNET DATABASE Lite•Browse•Advanced

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
* denotes mobile formatted website

Links to Resources

NLM Resources (File Locators)

Regulatory Agencies (Superlist Locators)

Other Resources (Internet Locators)


Search for this InChIKey on the Web

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) BEHAVIORAL: EXCITEMENT

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 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) CARDIAC: CHANGE IN RATE

PERIPHERAL NERVE AND SENSATION: PARESTHESIS

BEHAVIORAL: ATAXIA		 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.