YOHIMBE BARK EXTRACT [YOHIMBINE]

Yohimbe Bark extract [Yohimbine], also known as quebrachine, is an indole alkaloid derived from the bark of the African tree Pausinystalia johimbe; also from the bark of the unrelated South American tree Aspidosperma quebracho-blanco. 
Yohimbe Bark extract [Yohimbine] is an α2-adrenergic receptor antagonist, and has been used in a variety of research projects. 
Yohimbe Bark extract [Yohimbine] is a veterinary drug used to reverse sedation in dogs and deer.

CAS:    146-48-5
MF:    C21H26N2O3
MW:    354.44
EINECS:    205-672-0

Synonyms
;yohimbine;YOHIMBINE, C-;17alpha-Hydroxyyohimban-16alpha-carboxylic acid;17-alpha-hydroxy-yohimban-16-alpha-carboxylicacimethylester;17-Hydroxyyohimban-16-carboxylic acid methyl ester;17-hydroxyyohimban-16-carboxylicacidmethylester;Aphrodine;Aphrosol;Yohimbine;146-48-5;Yohimbin;Quebrachin;Corynine;Quebrachine;APHRODINE;Aphrosol;Yohimbic acid methyl ester;(+)-Yohimbine;Actibine;Johimbin;Yohimbinum;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-;EINECS 205-672-0;UNII-2Y49VWD90Q;BRN 0097276;2Y49VWD90Q;CCRIS 9415;17-Hydroxyyohimban-16-carboxylic acid methyl ester;DTXSID9040130;CHEBI:10093;methyl 17alpha-hydroxyyohimban-16alpha-carboxylate;CHEMBL15245;17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester;DTXCID7020130;(16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester;4-25-00-01237 (Beilstein Handbook Reference);methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^;{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate;CHEMBL537669;Yohimbine (DCF);CAS-146-48-5;methyl hydroxy[?]carboxylate;trans-Quinolizidine yohimbine;Yohimbe bark;SR-01000075297;Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.;MFCD00005093;Amberlite CG 400;NSC19509;YOHIMBINE [MI];Prestwick0_000584;Prestwick1_000584;Prestwick2_000584;Prestwick3_000584;Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester;YOHIMBINE [VANDF];YOHIMBINUM [HPUS];cid_6169;cid_8969;YOHIMBE HYDROCHLORIDE;YOHIMBINE [WHO-DD];Lopac0_001210;SCHEMBL33954;BSPBio_000428;BSPBio_001236;GTPL102;KBioGR_000576;KBioSS_00057;MLS000728591;SPBio_002647;BPBio1_000472;Yohimbol-16alpha-carboxylic acid, methyl ester (6CI);BCBcMAP01_000032;KBio2_000576;KBio2_003144;KBio2_005712;KBio3_001031;KBio3_001032;Bio1_000455;Bio1_000944;Bio1_001433;Bio2_000458;Bio2_000938;HMS1362N17;HMS1792N17;HMS1990N17;HMS2089G19;HMS2234C18;Tox21_110019;BDBM50013515;BDBM50203564;AKOS015902024;Tox21_110019_1;Yohimban-16-.alpha.-carboxylic acid, 17-.alpha.-hydroxy-, methyl ester;Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI);CCG-205284;CS-5173;DB01392;GS-5751;SDCCGSBI-0051177.P002;IDI1_002213;MRF-0000020;SMP1_000320;NCGC00013260-01;NCGC00025018-05;NCGC00025018-06;NCGC00025018-07;NCGC00025018-10;NCGC00025018-11;NCGC00025018-16;NCGC00025018-17;NCGC00025018-24;NCGC00025018-29;HY-12715;SMR000470778;17a-hydroxy-16a-methoxycarbonyl-yohimbane;NS00003970;C09256;D08685;H10057;EN300-19731915;Q412226;SR-01000075297-5;BRD-K35586044-001-02-6;BRD-K35586044-003-03-0;BRD-K35586044-003-11-3;BRD-K35586044-003-14-7;BRD-K35586044-003-15-4
17.ALPHA.-HYDROXY-20-.ALPHA.-YOHIMBAN-16-.BETA.-CARBOXYLIC ACID, METHYL ESTER;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)- (9CI)
(1R,2S,4aR,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo;[2'',3'':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester hydrochloride
103834-06-6;methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate

While Yohimbe Bark extract [Yohimbine] behaves as an aphrodisiac in some mammals, it does not do so in humans. 
Yohimbe Bark extract [Yohimbine] has been prescribed as a treatment for erectile dysfunction, although its reported clinical benefits were modest and it has largely been superseded by the PDE5 inhibitor class of drugs. 
Substances that have purported to be extracts from the yohimbe tree have been marketed as dietary supplements for various purposes, but they contain highly variable amounts of yohimbine, if any; no published scientific evidence supports their efficacy.
Yohimbe Bark extract [Yohimbine] is a competitive and selective 2-blocker. 
Yohimbe Bark extract [Yohimbine] is an indolealkylamine alkaloid and is found in the bark of thetree Pausinystalia yohimbe and in Rauwolfia root.
Yohimbe Bark extract [Yohimbine] is an indole alkaloid with alpha2-adrenoceptor antagonist activity. 
Yohimbe Bark extract [Yohimbine] is produced by Corynanthe johimbe and Rauwolfia serpentina. 
Yohimbe Bark extract [Yohimbine] has a role as an alpha-adrenergic antagonist, a serotonergic antagonist and a dopamine receptor D2 antagonist. 
Yohimbe Bark extract [Yohimbine] is functionally related to a yohimbic acid.

Yohimbe Bark extract [Yohimbine] is the name of an evergreen tree found in parts of central and western Africa. 
The bark of yohimbe contains a chemical called Yohimbe Bark extract [Yohimbine], which is used to make medicine. Yohimbe Bark extract [Yohimbine] is a form of yohimbine that is a prescription drug in the US.
Yohimbe Bark extract [Yohimbine] supplements often list yohimbe bark extract or yohimbine as the active ingredient. 
However, some of these products might not provide accurate information about the amount of yohimbine in the supplement. 
Also, some Yohimbe Bark extract [Yohimbine] supplements list yohimbine hydrochloride as an active ingredient. 
Yohimbe Bark extract [Yohimbine] products containing man-made yohimbine hydrochloride as an ingredient are not legal to sell as a dietary supplement in the US.Yohimbine powder
Yohimbe Bark extract [Yohimbine] is taken by mouth arouse sexual excitement, for erectile dysfunction (ED), sexual problems caused by medications for depression called selective-serotonin reuptake inhibitors (SSRIs), and general sexual problems in both men and women. 
Yohimbe Bark extract [Yohimbine] is also used for athletic performance, weight loss, exhaustion, chest pain, high blood pressure, low blood pressure that occurs when standing up, diabetic nerve pain, and for depression along with certain other medications.

Yohimbe Bark extract [Yohimbine] is a natural alkaloid. 
Yohimbe Bark extract [Yohimbine] was first extracted from the barks of Corynanthe yohimbe, a species of Rubiaceae trees in West Africa. 
Yohimbe Bark extract [Yohimbine] was reported that, in the dried bark of Pausinystalia johimbe, the content of mixed alkaloids is higher than 6.1%, in which the main component is yohimbine, indicating a great prospect for development.
Yohimbe Bark extract [Yohimbine] has been used as an aphrodisiac in Africa since ancient times. 
In 1900, Yohimbe Bark extract [Yohimbine] was applied by Kowit and Muller to patients with impotence and paralytic insensitivity caused by neurasthenia and obtained curative effect. 
From then on, clinical application of Yohimbe Bark extract [Yohimbine] began. 
Currently, v is a pure plant preparation in the treatment of erectile dysfunction with more affirmation and more applications.
Yohimbe Bark extract [Yohimbine] is an indole alkaloid with alpha2-adrenoceptor antagonist activity. 
Yohimbe Bark extract [Yohimbine] is produced by Corynanthe johimbe and Rauwolfia serpentina. 
Yohimbe Bark extract [Yohimbine] has a role as an alpha-adrenergic antagonist, a serotonergic antagonist and a dopamine receptor D2 antagonist. 
Yohimbe Bark extract [Yohimbine] is functionally related to a yohimbic acid.

Yohimbe Bark extract [Yohimbine] is an alpha 2 adrenergic receptor antagonist that has been shown to be a potent competitive antagonist at the 5-HT receptor. 
Yohimbe Bark extract [Yohimbine] has also been shown to have low potency as an α7 nicotinic acetylcholine receptor antagonist and to inhibit locomotor activity in vivo. 
In humans, Yohimbe Bark extract [Yohimbine] increases serum catecholamine levels, but does not affect blood pressure or heart rate. 
Yohimbe Bark extract [Yohimbine] has been shown to produce a dose-dependent inhibition of erythrocyte aggregation in vitro, and inhibits platelet aggregation in vitro and in vivo. 
Yohimbe Bark extract [Yohimbine] also inhibits human platelet aggregation induced by collagen or thrombin. 
Yohimbe Bark extract [Yohimbine] is a competitive antagonist of serotonin at the 5HT receptor, but it also has low potency as an α7 nicotinic acetylcholine receptor antagonist and it inhibits locomotor activity in vivo. 

Yohimbe Bark extract [Yohimbine] Chemical Properties
Melting point: 231-233 °C(lit.)
Alpha: D20 +50.9 to +62.2° (ethanol); D20 +108° (pyridine); 20546 +129° (c = 0.5 in pyridine)
Boiling point: 487.66°C (rough estimate)
Density: 1.1640 (rough estimate)
Refractive index: 1.6500 (estimate)
Storage temp.: Sealed in dry,Room Temperature
Solubility: THF; DMSO; Chloroform;
Form: Solid
pka: 14.39±0.40(Predicted)
Color: Beige
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/s1
InChIKey: BLGXFZZNTVWLAY-SCYLSFHTSA-N
LogP: 2.730
CAS DataBase Reference: 146-48-5(CAS DataBase Reference)
NIST Chemistry Reference: Yohimbe Bark extract [Yohimbine](146-48-5)

Appearance: white powder. 
Solubility: soluble in ethanol, chloroform, and hot benzene; slightly soluble in water and ether, usually salified by hydrochloric acid to increase its solubility in water. 
Specific rotatory power (°): D22 +105° (in water). 
Melting point: 241–246?°C.
Glistening, needle-like alkaloid, soluble in alcohol and ether, very slightly soluble in water.

Uses    
Yohimbe Bark extract [Yohimbine] occurs in Corinanthe johimbeK. and Rubiaceae trees. 
Yohimbe Bark extract [Yohimbine] is also foundin the roots of Rauwolfia serpentina L.and Apocyanaceae. 
Yohimbe Bark extract [Yohimbine]'s derivatives areused therapeutically as adrenergic blockingagents.
Obtained from leaves and bark of Corynanthe johimbe. 
Formerly used as an aphrodisiac in veterinary medicine, Yohimbe Bark extract [Yohimbine] works primarily by acting as an antagonist at α2-adrenergic receptors.
Yohimbe Bark extract [Yohimbine] increases heart rate and blood pressure as aresult of its blockade of 2-receptors in the CNS. 
Yohimbe Bark extract [Yohimbine] has beenused experimentally to treat male erectile impotence.
Yohimbe Bark extract [Yohimbine] is a drug used in veterinary medicine to reverse the effects of xylazine in dogs and deer.
Yohimbe Bark extract [Yohimbine] is used as a research reagent. 
In the US, Yohimbe Bark extract [Yohimbine] is prescribed, but now rarely, for erectile dysfunction in men.

Pharmacology    
Studies have shown that yohimbine has extensive pharmacological effects and has been developed for the clinical treatment of arteriosclerosis, rheumatism, and other diseases. 
The most obvious pharmacological action is in the treatment of male sexual dysfunction. 
Yohimbine tablets have been approved by the FDA and circulate in international markets. 
Yohimbine can selectively block the presynaptic alpha 2 receptors and promote the release of norepinephrine. 
Yohimbe Bark extract [Yohimbine] stimulates more norepinephrine released by cavernous nerve endings and reduces reflux of phallic vein, which is conducive to congestive erection. 
A small amount of application can make the perineum swell and stimulate the erection center at the spinal cord, leading to sexual hyperfunction. 
Yohimbe Bark extract [Yohimbine] also has a psychological stimulant effect and increases libido. 
Like other types of adrenergic blocking drugs, Yohimbe Bark extract [Yohimbine]’s resistance to adrenergic mediator in blood circulation is much stronger than to sympathetic nerve impulse. 
Again, like tolazoline, Yohimbe Bark extract [Yohimbine] shows slight effect in resisting adrenergic response in ocular smooth muscle. 
This drug does not block the frequency and inotropic effects of epinephrine on mammalian hearts. 
Yohimbe Bark extract [Yohimbine] has minor direct effects on smooth muscle, and its effect on the central nervous system is far less than that of ergot alkaloids, because yohimbine performs an excited-to-paralyzed action. 
This drug produces diuretic effect, probably due to the stimulation of the hypothalamus, resulting in release of posterior pituitary hormone. 
In addition, Yohimbe Bark extract [Yohimbine] has a significant local anesthetic effect.

Effectiveness    
There is mixed evidence about the effectiveness of Yohimbe Bark extract [Yohimbine], the active ingredient in yohimbe, for treating anxiety related to phobias. 
Some research suggests that Yohimbe Bark extract [Yohimbine] does not improve anxiety when combined with therapy. 
However, other research suggests that Yohimbe Bark extract [Yohimbine] reduces fear related to certain phobias.
Early research suggests that taking Yohimbe Bark extract [Yohimbine], the active ingredient of yohimbe, daily for 10 days does not improve depression symptoms.
There is evidence that yohimbine, the active ingredient of yohimbe, can be helpful for ED. 
Some herbalists suggest that the Yohimbe Bark extract [Yohimbine] actually works better than the yohimbine ingredient alone. 
However, so far yohimbe bark has not been evaluated in research studies.
Exercise performance. 
Early research suggests that taking Yohimbe Bark extract [Yohimbine], the active ingredient in yohimbe, daily for 21 days does not improve exercise performance or build muscle mass in soccer players.

Head rush (orthostatic hypotension). 
Early research suggests that taking a single dose of Yohimbe Bark extract [Yohimbine], the active ingredient in yohimbe, increases blood pressure in people with a head rush due to low blood pressure. 
However, other early research suggests that Yohimbe Bark extract [Yohimbine] does not improve blood pressure.
Sexual problems caused by selective-serotonin reuptake inhibitors (SSRIs). 
There is evidence from many studies that yohimbine, the active ingredient of yohimbe, can improve sexual problems associated with this class of medications used for depression. 
However, this benefit has not been described specifically for the yohimbe bark.
Early research suggests that taking Yohimbe Bark extract [Yohimbine], the active ingredient in yohimbe, improves symptoms of dry mouth in people taking antidepressants. 
The effect of the yohimbe bark on dry mouth is not clear.

Side Effects    
Yohimbe Bark extract [Yohimbine], taken by mouth, is POSSIBLY UNSAFE. 
Yohimbe Bark extract [Yohimbine] has been linked to reports of severe side effects including irregular or rapid heart beat, kidney failure, seizure, heart attack, and others.
The primary active ingredient in yohimbe is a drug called yohimbine. 
Yohimbe Bark extract [Yohimbine] is considered a prescription drug in North America. 
Yohimbe Bark extract [Yohimbine] drug can be safely used short-term when monitored by a health professional.
However, Yohimbe Bark extract [Yohimbine] is not appropriate for unsupervised use due to potentially serious side effects that it can cause.
Children should not take yohimbe. 
Yohimbe Bark extract [Yohimbine] is POSSIBLY UNSAFE for children because children appear to be extra sensitive to the harmful effects of yohimbe.
When taken by mouth in typical doses, yohimbe and the ingredient yohimbine can cause stomach upset, excitation, tremor, sleep problems, anxiety or agitation, high blood pressure, a racing heartbeat, dizziness, stomach problems, drooling, sinus pain, irritability, headache, frequent urination, bloating, rash, nausea, and vomiting.
Taking high doses can also cause other severe problems, including difficulty breathing, paralysis, very low blood pressure, heart problems, and death. 
After taking a one-day dose of yohimbine, one person reported an allergic reaction involving fever; chills; listlessness; itchy, scaly skin; progressive kidney failure; and symptoms that looked like the auto-immune disease called lupus.