| Name: | methyl(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride |
| CAS Number: | 65-19-0 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 200-600-4 |
| FDA UNII: | NB2E1YP49F |
| MDL: | MFCD00012674 |
| Molecular Weight: | 390.90979000 |
| Formula: | C21 H27 Cl N2 O3 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Melting Point: | 289.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 543.00 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 540.00 °F. TCC ( 282.20 °C. ) (est)
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| logP (o/w): | 2.201 (est) |
| Soluble in: |
| | water, 7300 mg/L @ 20 °C (exp) | | | water, 790.3 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
parenteral-frog LD50 26 mg/kg
Bulletin des Sciences Pharmacologiques. Vol. 47, Pg. 33, 1940.
intraperitoneal-guinea pig LD50 42 mg/kg
Bulletin des Sciences Pharmacologiques. Vol. 47, Pg. 33, 1940.
oral-man TDLo 133 ug/kg
BEHAVIORAL: EUPHORIA
American Journal of Psychiatry. Vol. 141, Pg. 1267, 1984.
intraperitoneal-mouse LD50 45 mg/kg
United States Patent Document. Vol. #4179510
oral-mouse LD50 40 mg/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Pharmaceutical Sciences. Vol. 51, Pg. 345, 1962.
intravenous-mouse LDLo 15 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 50, Pg. 241, 1935.
intravenous-rabbit LDLo 5 mg/kg
"Zur Pharmakologie der Yohimbealkaloide, Dissertation," Langer, J., Institute fuer Pharmakologie und Experimentelle Therapie der Universitat Breslau, Poland, 1932Vol. -, Pg. -, 1932.
intraperitoneal-rat LD50 55 mg/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.
|
| Dermal Toxicity: |
subcutaneous-dog LDLo 20 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
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.
subcutaneous-frog LD50 34 mg/kg
Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 137, Pg. 305, 1943.
subcutaneous-mouse LD50 43900 ug/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.
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for yohimbine hydrochloride usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for yohimbine hydrochloride flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
| EPI System: View |
| ClinicalTrials.gov:search |
| Daily Med:search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):65-19-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6169 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| methyl(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride |
| Chemidplus:0000065190 |
| RTECS:ZG1015000 for cas# 65-19-0 |
References:
| | methyl(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 6169 |
| Pubchem (sid): | 134972470 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | antagonil | | | aphrodine hydrochloride | | | aphrodyne | | (16a,17a)-17- | hydroxyyohimban-16-carboxylate de méthyle chlorhydrate | | | methyl (16a,17a)-17-hydroxyyohimban-16-carboxylate hydrochloride (1:1) | | | methyl (1R,2S,4aR,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate hydrochloride | | | methyl(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride | | | yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16a,17a)-, hydrochloride (1:1) | | | yohimban-16a-carboxylic acid, 17a-hydroxy-, methyl ester, monohydrochloride | | | yohimbin hydrochloride | | | yohimbine monohydrochloride | | | yohimbine.HCl | | | yohimbinehydrochloride |
Articles:
| PubMed:Enhancing exposure therapy for anxiety disorders, obsessive-compulsive disorder and post-traumatic stress disorder. |
| PubMed:Enhancing exposure therapy for PTSD with yohimbine HCL: protocol for a double-blind, randomized controlled study implementing subjective and objective measures of treatment outcome. |
| PubMed:The role of α₂ adrenoceptor in mediating noradrenaline action in the ventrolateral orbital cortex on allodynia following spared nerve injury. |
| PubMed:Case study: two fatal case reports of acute yohimbine intoxication. |
| PubMed:A validated high performance thin layer chromatography method for determination of yohimbine hydrochloride in pharmaceutical preparations. |
| PubMed:Non-Antidepressant Psychopharmacologic Treatment of Specific Phobias. |
| PubMed:Potential effects of yohimbine and sildenafil on erectile dysfunction in rats. |
| PubMed:Dexmedetomidine administration before, but not after, ischemia attenuates intestinal injury induced by intestinal ischemia-reperfusion in rats. |
| PubMed:Does yohimbine hydrochloride facilitate fear extinction in virtual reality treatment of fear of flying? A randomized placebo-controlled trial. |
| PubMed:Molecular structure, vibrational spectra and HOMO, LUMO analysis of yohimbine hydrochloride by density functional theory and ab initio Hartree-Fock calculations. |
| PubMed:Effect of the α(2)-adrenoceptor antagonist yohimbine on vascular regulation of the middle cerebral artery and the ophthalmic artery in healthy subjects. |
| PubMed:Antidepressant-like effects of glucagon-like peptide-2 in mice occur via monoamine pathways. |
| PubMed:Platelet responsiveness to yohimbine hydrochloride and MRS2179 in the context of the interaction between collagen and epinephrine in acute coronary syndrome. |
| PubMed:Facilitation of fear extinction in phobic participants with a novel cognitive enhancer: a randomized placebo controlled trial of yohimbine augmentation. |
| PubMed:The antiallodynic effect of Neurotropin is mediated via activation of descending pain inhibitory systems in rats with spinal nerve ligation. |
| PubMed:Effects of a supplement designed to increase ATP levels on muscle strength, power output, and endurance. |
| PubMed:Baroreflex sensitivity associated hypoalgesia in healthy states is altered by chronic pain. |
| PubMed:The relationship between resting blood pressure and acute pain sensitivity: effects of chronic pain and alpha-2 adrenergic blockade. |
| PubMed:Anesthesia induced by administration of xylazine hydrochloride alone or in combination with ketamine hydrochloride and reversal by administration of yohimbine hydrochloride in captive Axis deer (Axis axis). |
| PubMed:Effects of brimonidine ingestion on cardiovascular responses and renal function in conscious dogs. |
| PubMed:Structural insights in platelet receptor synergism-antiplatelet therapy in post-ischemic cerebrovascular events. |
| PubMed:Insensitivity to the alpha2-adrenergic receptor blocker yohimbine hydrochloride and occurrence of spontaneous platelet macroaggregation (SPMA) in diabetes. |
| PubMed:Behavioral reactivity to a noradrenergic challenge after chronic oral methylphenidate (ritalin) in rats. |
| PubMed:A comparison of carfentanil/xylazine and Telazol/xylazine for immobilization of white-tailed deer. |
| PubMed:Efficacy and safety of a novel combination of L-arginine glutamate and yohimbine hydrochloride: a new oral therapy for erectile dysfunction. |
| PubMed:Methadone patients exhibit increased startle and cortisol response after intravenous yohimbine. |
| PubMed:Comparison of the effects of clonidine and yohimbine on spontaneous pupillary fluctuations in healthy human volunteers. |
| PubMed:Comparison of tympanic membrane and rectal temperatures of anesthetized fallow deer (Dama dama) |
| PubMed:Effect of alpha 2-adrenergic, cholinergic, and nonsteroidal anti-inflammatory drugs on myoelectric activity of ileum, cecum, and right ventral colon and on cecal emptying of radiolabeled markers in clinically normal ponies. |
| PubMed:Therapeutic effects of high dose yohimbine hydrochloride on organic erectile dysfunction. |
| PubMed:Double-blind, placebo-controlled safety and efficacy trial with yohimbine hydrochloride in the treatment of nonorganic erectile dysfunction. |
| PubMed:Noradrenergic and serotonergic function in posttraumatic stress disorder. |
| PubMed:Yohimbine elimination in normal volunteers is characterized by both one- and two-compartment behavior. |
| PubMed:Is high-dose yohimbine hydrochloride effective in the treatment of mixed-type impotence? A prospective, randomized, controlled double-blind crossover study. |
| PubMed:Effects of a carfentanil-xylazine combination on cardiopulmonary function and plasma catecholamine concentrations in female bongo antelopes. |
| PubMed:Field immobilization of muskrats (Ondatra zibethicus) for minor surgical procedures. |
| PubMed:Effects of yohimbine on autonomic measures are determined by individual values for area under the concentration-time curve. |
| PubMed:Pavlovian conditioning to a diazepam cue with yohimbine as the unconditional stimulus. |
| PubMed:Antagonism of xylazine in white-tailed deer with intramuscular injection of yohimbine. |
| PubMed:Effects of Alzheimer's disease and normal aging on cerebrospinal fluid norepinephrine responses to yohimbine and clonidine. |
| PubMed:[Central ocular hypotensive effect of noradrenaline]. |
| PubMed:Immobilization of Rocky Mountain elk with Telazol and xylazine hydrochloride, and antagonism by yohimbine hydrochloride. |
| PubMed:Erectile dysfunction. Are you prepared to discuss it? |
| PubMed:Noradrenergic response to acute ethanol administration in healthy subjects: comparison with intravenous yohimbine. |
| PubMed:Specificity of ethanollike effects elicited by serotonergic and noradrenergic mechanisms. |
| PubMed:Noradrenergic dysregulation during discontinuation of cocaine use in addicts. |
| PubMed:Postpartum immobilization of adult female moose using xylazine, ketamine and yohimbine hydrochlorides. |
| PubMed:Response of post-ischemic myocardium to sympathetic stimulation--relation to local norepinephrine release. |
| PubMed:Abnormal noradrenergic function in posttraumatic stress disorder. |
| PubMed:Effects of yohimbine as a reversing agent for ketamine-xylazine anesthesia in budgerigars. |
| PubMed:Ventricular wall motion and NE release in post-ischemic reperfused myocardium. |
| PubMed:Central effects of yohimbine on copulatory behavior in aged male rats. |
| PubMed:Dose-response effects of oral yohimbine in unrestrained primates. |
| PubMed:Effects of clonidine and yohimbine on the pupillary light reflex and carbachol-evoked sweating in healthy volunteers. |
| PubMed:Immobilization of gray wolves (Canis lupus) with sufentanil citrate. |
| PubMed:Effects of yohimbine on bradycardia and duration of recumbency in ketamine/xylazine anesthetized ferrets. |
| PubMed:Yohimbine bioavailability in humans. |
| PubMed:Adrenoceptor specificity in the central regulation of adrenocortical secretion. |
| PubMed:Effect of yohimbine hydrochloride on erectile impotence: a double-blind study. |
| PubMed:Yohimbine reversal of ketamine-xylazine immobilization of raccoons (Procyon lotor). |
| PubMed:Intravenous yohimbine. Selective enhancer of norepinephrine and cortisol secretion and systolic blood pressure in humans. |
| PubMed:Involvement of a central nervous pathway in yohimbine-induced insulin secretion. |
| PubMed:Physiological response of gray wolves to butorphanol-xylazine immobilization and antagonism by naloxone and yohimbine. |
| PubMed:Antagonism of xylazine hydrochloride sedation in raptors by yohimbine hydrochloride. |
| PubMed:Use of xylazine sedation with yohimbine antagonism in captive gray wolves. |
| PubMed:alpha 2-Adrenergic receptor sensitivity in depression. The plasma MHPG, behavioral, and cardiovascular responses to yohimbine. |
| PubMed:Ketamine-xylazine anesthesia in red-tailed hawks with antagonism by yohimbine. |
| PubMed:Comparative pharmacokinetics of yohimbine in steers, horses and dogs. |
| PubMed:Immobilization of white-tailed deer by etorphine and xylazine and its antagonism by nalmefene and yohimbine. |
| PubMed:Rapid reversible immobilization of feral stallions using etorphine hydrochloride, xylazine hydrochloride and atropine sulfate. |
| PubMed:Cardiovascular and behavioral responses of gray wolves to ketamine-xylazine immobilization and antagonism by yohimbine. |
| PubMed:Antagonism of xylazine hydrochloride-ketamine hydrochloride immobilization in guineafowl (Numida meleagris) by yohimbine hydrochloride. |
| PubMed:Yohimbine hydrochloride reversal of ketamine hydrochloride and xylazine hydrochloride immobilization of Bengal tigers and effects on hematology and serum chemistries. |
| PubMed:The pharmacokinetics of yohimbine in man. |
| PubMed:Desipramine-yohimbine combination treatment of refractory depression. Implications for the beta-adrenergic receptor hypothesis of antidepressant action. |
| PubMed:Alpha 2-adrenergic and opiate receptor blockade. Synergistic effects on anxiety in healthy subjects. |
| PubMed:Immobilization of coyotes with xylazine hydrochloride-ketamine hydrochloride and antagonism by yohimbine hydrochloride. |
| PubMed:Failure of yohimbine hydrochloride to antagonize ketamine hydrochloride immobilization of gray wolves. |
| PubMed:Alpha 2-adrenergic receptor function in depression. The cortisol response to yohimbine. |
| PubMed:Effect of caffeine sodium benzoate, ketamine hydrochloride, and yohimbine hydrochloride on xylazine hydrochloride-induced anorexia in white-tailed deer. |
| PubMed:Determination of yohimbine hydrochloride in horse serum using high-performance liquid chromatography. |
| PubMed:Effect of yohimbine hydrochloride on serum prolactin concentration in the rat: possible antagonist for fescue toxicosis. |
| PubMed:Effects on fawn survival of multiple immobilizations of captive pregnant white-tailed deer. |
| PubMed:Antagonism of xylazine hydrochloride with yohimbine hydrochloride and 4-aminopyridine in captive wapiti. |
| PubMed:Yohimbine hydrochloride as an antagonist to xylazine hydrochloride-ketamine hydrochloride immobilization of white-tailed deer. |
| PubMed:Use of yohimbine hydrochloride to reverse immobilization of polar bears by ketamine hydrochloride and xylazine hydrochloride. |
| PubMed:Failure of yohimbine to reverse ketamine anesthesia in rhesus monkeys. |
| PubMed:Studies on the mechanism of clonidine-induced mydriasis in the rat. |
| PubMed:Yohimbine and the model anxiety state. |
| PubMed:Enhancement of sexual motivation in male rats by yohimbine. |
| PubMed:CNS adrenergic inhibition of parasympathetic oculomotor tone. |
| PubMed:Evidence for two distinct sympathoinhibitory bulbo-spinal systems. |
| PubMed:Use of a sympathetic-cholinergic system in the analysis of sympatho-inhibition produced by clonidine and some congeneric derivatives of clonidine. |
| PubMed:Antagonism of xylazine sedation by 4-aminopyridine and yohimbine in cattle. |
| PubMed:Analysis of pupillary dilation produced by analogs of clonidine. |
| PubMed:Methyldopa produces central inhibition of parasympathetic activity in the cat. |
| PubMed:[Favorable effect of yohimbine hydrochloride on orthostatic hypotension induced by clomipramine]. |
| PubMed:Potentiation of two sympathetic reflexes by yohimbine hydrochloride. |
| PubMed:Analysis of clonidine-induced mydriasis. |
| PubMed:Autonomic and psychic effects of yohimbine hydrochloride. |
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