OXOTREMORINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H18N2O
Molecular Weight	206.2841
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1CCCN1CC#CCN2CCCC2

InChI

InChIKey=RSDOPYMFZBJHRL-UHFFFAOYSA-N

InChI=1S/C12H18N2O/c15-12-6-5-11-14(12)10-4-3-9-13-7-1-2-8-13/h1-2,5-11H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68010095 | https://www.ncbi.nlm.nih.gov/pubmed/8330013 | https://www.ncbi.nlm.nih.gov/pubmed/14020934

Oxotremorine, a metabolite of tremorine, is a non-hydrolyzed muscarinic acetylcholine receptor agonist used as a research tool. This compound is a muscarinic agent equal in potency to acetylcholine, but completely lacking in nicotinic activity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Agonist 2678	5.48 null [pKi]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Agonist 2678	5.03 null [pKi]
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Agonist 2678	5.28 null [pKi]
Muscarinic acetylcholine receptor M4 86 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Agonist 2678	5.15 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
[Tremor following intracerebral carbachol injection. 1.Carbachol sensitivity of various brain structures].	1975	1189819
Hypokalemia with syncope caused by habitual drinking of oolong tea.	1999 Mar	10337936
Effects of ropinirole on various parkinsonian models in mice, rats, and cynomolgus monkeys.	2000 Mar	10683491
Elucidating the role of muscarinic receptors in psychosis.	2001 Apr 27	11392633
Identification of subtypes of muscarinic receptors that regulate Ca2+ and K+ channel activity in sympathetic neurons.	2001 Apr 27	11392616
Modulation of electrically evoked acetylcholine release in cultured rat septal neurones.	2001 Jan	11208918
Cannabinoid CB1 receptor-mediated inhibition of acetylcholine release in the brain of NMRI, CD-1 and C57BL/6J mice.	2001 Jan	11191836
K(ATP) channel blockers selectively interact with A(1)-adenosine receptor mediated modulation of acetylcholine release in the rat hippocampus.	2001 Jan 19	11166687
Central muscarinic mechanisms regulating voiding in rats.	2001 Jun	11356913
Reversal of morphine-induced memory impairment in mice by withdrawal in Morris water maze: possible involvement of cholinergic system.	2001 Mar	11325406
Receptor reserve of phosphoinositide-coupled muscarinic receptors in mouse hippocampus in vivo.	2001 Oct 19	11597604
The role of nitric oxide in the reversal of hemorrhagic shock by oxotremorine.	2001 Oct 5	11675044
Intravenously administered oxotremorine and atropine, in doses known to affect pain threshold, affect the intraspinal release of acetylcholine in rats.	2002 Apr	12076312
Parkinson's disease risks associated with cigarette smoking, alcohol consumption, and caffeine intake.	2002 Apr 15	11943691
Evaluation of the central properties of several Hypericum species from the Canary Islands.	2002 Dec	12458477
Age-related effects of chlorpyrifos on muscarinic receptor-mediated signaling in rat cortex.	2002 Jan	11876500
Presynaptic muscarinic M(2)-receptor-mediated inhibition of N-type Ca(2+) channels in cultured sphenopalatine ganglion: direct evidence for acetylcholine inhibition of cerebral nitrergic neurogenic vasodilation.	2002 Jul	12065743
M1 muscarinic receptor signaling in mouse hippocampus and cortex.	2002 Jul 19	12106668
Modulation by adenosine of both muscarinic M1-facilitation and M2-inhibition of [3H]-acetylcholine release from the rat motor nerve terminals.	2002 Jun	12081652
The spinal antinociceptive effects of cholinergic drugs in rats: receptor subtype specificity in different nociceptive tests.	2002 Nov 19	12441008
Role of muscarinic receptors in the activation of the ventral subiculum and the consequences for dopamine release in the nucleus accumbens.	2003 Jan 24	12559371
Cholinergic regulation of pericyte-containing retinal microvessels.	2003 Jun	12560212
A beta-induced TNF-alpha expression and acetylcholine action in mouse glial cells.	2003 Mar 28	12628466
Presynaptic modulation of acetylcholine, noradrenaline, and serotonin release in the hippocampus of aged rats with various levels of memory impairments.	2003 May 15	12754090

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Pretreatment of the guinea-pig ileal longitudinal muscle tissue with 10^-7 - 10^-5 M oxotremorine (desensitizing treatment) in normal Tyrode solution caused desensitization of the responses to acetylcholine (ACh), as did the desensitizing treatment with ACh. However, Ca2+-free conditions significantly reduced oxotremorine-induced desensitization, contrary to the previous findings that Ca2+-free conditions enhanced ACh-induced desensitization. The desensitizing treatment with oxotremorine caused suppression of the responses to high K+ (tonic phase), as did the ACh treatment. Ca2+-free conditions removed this suppression, whereas this condition enhanced ACh-induced suppression of the K+ response. A protein kinase C inhibitor, 1-(5-isoquinolinesulfonyl)-2-methylpiperazine (10^-4 M) had no effect on oxotremorine-induced desensitization of the ACh response. The results suggest that a voltage-gated Ca2+ channel was involved in oxotremorine-induced desensitization, as in ACh-induced desensitization, but that the process of inactivation of Ca2+ channels was different between oxotremorine and ACh, and that oxotremorine-induced desensitization was due not only to Ca2+ channel, but also to other unknown factors. Protein kinase C did not participate in oxotremorine-induced desensitization.

Name

Type

Language

OXOTREMORINE

Common Name

English

1-(2-OXOPYRROLIDINO)-4-PYRROLIDINO-2-BUTYNE

Systematic Name

English

NSC-330497

Code

English

OXOTREMORINE [MI]

Common Name

English

OXYTREMORINE

Common Name

English

Code System Code Type Description

FDA UNII

5RY0UWH1JL