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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
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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/s1InChIKey
BLGXFZZNTVWLAY-SCYLSFHTSA-NSmiles
COC(=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.