Yohimbine

(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

Formula: C21H26N2O3 (354.1943)
Chinese Name: 安慰乐得, 萎必治, 育亨宾, 异柯楠碱
BioDeep ID: BioDeep_00000000695 ( View LC/MS Profile)
SMILES: [H][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2



Found 31 Sample Hits

m/z Adducts Species Organ Scanning Sample
393.2911 [M+K]+
PPM:2.5
Vitis vinifera Fruit MALDI (DHB)
grape_dhb_91_1 - Grape Database
Resolution: 50μm, 120x114

Description

Grape berries fruit, condition: Ripe

393.2948 [M+K]+
PPM:6.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_46 - MTBLS58
Resolution: 17μm, 298x106

Description

393.2911 [M+K]+
PPM:2.5
Vitis vinifera Fruit MALDI (DHB)
grape_dhb_163_1 - Grape Database
Resolution: 17μm, 132x115

Description

Grape berries fruit, condition: Late

393.2968 [M+K]+
PPM:12
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_47 - MTBLS58
Resolution: 17μm, 301x111

Description

393.2951 [M+K]+
PPM:7.7
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_03 - MTBLS58
Resolution: 17μm, 159x110

Description

337.1863 [M+H-H2O]+
PPM:14.1
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

319.1767 [M+H-2H2O]+
PPM:11.8
Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

337.1872 [M+H-H2O]+
PPM:11.4
Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

355.1955 [M+H]+
PPM:17.2
Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

337.1846 [M+H-H2O]+
PPM:19.1
Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

355.195 [M+H]+
PPM:18.6
Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

355.1967 [M+H]+
PPM:13.8
Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

337.1904 [M+H-H2O]+
PPM:1.9
Homo sapiens colorectal adenocarcinoma DESI ()
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415
Resolution: 17μm, 137x136

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

355.2009 [M+H]+
PPM:2
Homo sapiens colorectal adenocarcinoma DESI ()
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415
Resolution: 17μm, 137x136

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

337.1876 [M+H-H2O]+
PPM:10.2
Homo sapiens colorectal adenocarcinoma DESI ()
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415
Resolution: 17μm, 147x131

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

337.1898 [M+H-H2O]+
PPM:3.7
Homo sapiens colorectal adenocarcinoma DESI ()
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415
Resolution: 17μm, 157x136

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

355.1995 [M+H]+
PPM:5.9
Homo sapiens colorectal adenocarcinoma DESI ()
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415
Resolution: 17μm, 157x136

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

337.1844 [M+H-H2O]+
PPM:19.7
Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

355.1948 [M+H]+
PPM:19.2
Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

337.185 [M+H-H2O]+
PPM:17.9
Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

337.1858 [M+H-H2O]+
PPM:15.6
Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

337.1847 [M+H-H2O]+
PPM:18.8
Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

355.1953 [M+H]+
PPM:17.8
Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

337.1849 [M+H-H2O]+
PPM:18.2
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

355.1965 [M+H]+
PPM:14.4
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

337.1844 [M+H-H2O]+
PPM:19.7
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

337.1861 [M+H-H2O]+
PPM:14.7
Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description

355.1966 [M+H]+
PPM:14.1
Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description

355.1948 [M+H]+
PPM:19.2
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

337.1844 [M+H-H2O]+
PPM:19.7
Homo sapiens colorectal adenocarcinoma DESI ()
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176
Resolution: 50μm, 132x136

Description

355.1954 [M+H]+
PPM:17.5
Homo sapiens colorectal adenocarcinoma DESI ()
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176
Resolution: 50μm, 132x136

Description


Yohimbine is an indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina. It has a role as an alpha-adrenergic antagonist, a serotonergic antagonist and a dopamine receptor D2 antagonist. It is functionally related to a yohimbic acid. A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac. Yohimbine is an indole alkaloid derived from the bark of the Central African yohimbe tree (Pausinystalia yohimbe) that is widely used as therapy for erectile dysfunction. Yohimbine use has been associated with occasional severe adverse events, but has not been linked to serum enzyme elevations or clinically apparent acute liver injury. Yohimbine is a natural product found in Rauvolfia yunnanensis, Tabernaemontana corymbosa, and other organisms with data available. A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION. See also: Yohimbine Hydrochloride (active moiety of) ... View More ... Yohimbine is only found in individuals that have used or taken this drug. It is a plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac. [PubChem]Yohimbine is a pre-synaptic alpha 2-adrenergic blocking agent. The exact mechanism for its use in impotence has not been fully elucidated. However, yohimbine may exert its beneficial effect on erectile ability through blockade of central alpha 2-adrenergic receptors producing an increase in sympathetic drive secondary to an increase in norepinephrine release and in firing rate of cells in the brain noradrenergic nuclei. Yohimbine-mediated norepinephrine release at the level of the corporeal tissues may also be involved. In addition, beneficial effects may involve other neurotransmitters such as dopamine and serotonin and cholinergic receptors. G - Genito urinary system and sex hormones > G04 - Urologicals > G04B - Urologicals > G04BE - Drugs used in erectile dysfunction An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina. C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C72900 - Adrenergic Antagonist D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D018674 - Adrenergic Antagonists D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics D000089162 - Genitourinary Agents > D064804 - Urological Agents D001697 - Biomedical and Dental Materials > D003764 - Dental Materials Yohimbine is a potent and relatively nonselective alpha 2-adrenergic receptor (AR) antagonist, with IC50 of 0.6 μM. IC50 value: 0.6 uM [1] Target: alpha 2-adrenergic receptor in vitro: Yohimbine inhibits alpha2-receptor antagonist with Ki of 1.05 nM, 1.19 nM, and 1.19 nM for α2A, α2B, α2C, respectively. Yohimbine also inhibits 5-HT1B with Ki of 19.9 nM. Yohimbine acts to block the lowering of cAMP by alpha-2 adrenoceptor agonists. yohimbine actually causes a pronounced lowering of tyrosinase activity. [3] in vivo: Yohimbine is an antagonist at alpha2-noradrenaline receptors with putative panicogenic effects in human subjects, was administered to Swiss-Webster mice at doses of 0.5, 1.0, and 2.0 mg/kg. Yohimbine potentiates active defensive responses to threatening stimuli in Swiss-Webster mice.[2] Yohimbine is a potent and relatively nonselective alpha 2-adrenergic receptor (AR) antagonist, with IC50 of 0.6 μM. IC50 value: 0.6 uM [1] Target: alpha 2-adrenergic receptor in vitro: Yohimbine inhibits alpha2-receptor antagonist with Ki of 1.05 nM, 1.19 nM, and 1.19 nM for α2A, α2B, α2C, respectively. Yohimbine also inhibits 5-HT1B with Ki of 19.9 nM. Yohimbine acts to block the lowering of cAMP by alpha-2 adrenoceptor agonists. yohimbine actually causes a pronounced lowering of tyrosinase activity. [3] in vivo: Yohimbine is an antagonist at alpha2-noradrenaline receptors with putative panicogenic effects in human subjects, was administered to Swiss-Webster mice at doses of 0.5, 1.0, and 2.0 mg/kg. Yohimbine potentiates active defensive responses to threatening stimuli in Swiss-Webster mice.[2]