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

Molecular Formula	C12H18N2O
Molecular Weight	206.2841
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
[Behavior pharmacology of maprotiline, a new antidepressant].	1975 Nov	1240830
[Effect of tea polyphenols and tea pigments on inducing the activity of phase II detoxicating enzymes and on the chemoprevention of liver precancerous lesions].	2000 May 30	12725062
Validation of a new computerized system for recording and analysing drug-induced tremor in rats.	2001 Nov-Dec	12183189
Medical prevention of space motion sickness--animal model of therapeutic effect of a new medicine on motion sickness.	2002	12528715
Behavioral sensitization to amphetamine induced by a single i.p. dose of oxotremorine in the rat.	2002	12201037
Intravenously administered oxotremorine and atropine, in doses known to affect pain threshold, affect the intraspinal release of acetylcholine in rats.	2002 Apr	12076312
Activation of histaminergic H3 receptors in the rat basolateral amygdala improves expression of fear memory and enhances acetylcholine release.	2002 Aug	12193196
Multiple muscarinic acetylcholine receptor subtypes modulate striatal dopamine release, as studied with M1-M5 muscarinic receptor knock-out mice.	2002 Aug 1	12151512
Cholinergic activation of the basolateral amygdala regulates unlearned freezing behavior in rats.	2002 Aug 21	12191818
Evaluation of the central properties of several Hypericum species from the Canary Islands.	2002 Dec	12458477
Cholinergic modulation of basal and amphetamine-induced dopamine release in rat medial prefrontal cortex and nucleus accumbens.	2002 Dec 20	12468043
Monoaminergic and cholinergic stimulation of masculine sexual behavior in neonatally demasculinized male rats.	2002 Jul	12208122
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
Muscarinic receptors of the neostriatum--their role in controlling operant behavior in dogs.	2002 Jul-Aug	12243260
Modulation by adenosine of both muscarinic M1-facilitation and M2-inhibition of [3H]-acetylcholine release from the rat motor nerve terminals.	2002 Jun	12081652
Modulation of working memory and of long- but not short-term memory by cholinergic mechanisms in the basolateral amygdala.	2002 Mar	11981229
Phthalic acid amygdalopetal lesion of the nucleus basalis magnocellularis induces reversible memory deficits in rats.	2002 May	11991764
Modulation of ANP-C receptor signaling by endothelin-1 in A-10 smooth muscle cells.	2002 May 15	12054468
Amygdala modulation of memory consolidation: interaction with other brain systems.	2002 Nov	12559833
Streptozotocin-induced diabetes impairs G-protein linked signal transduction in vascular smooth muscle.	2002 Nov	12487372
Evaluation of muscarinic agonist-induced analgesia in muscarinic acetylcholine receptor knockout mice.	2002 Nov	12391271
The spinal antinociceptive effects of cholinergic drugs in rats: receptor subtype specificity in different nociceptive tests.	2002 Nov 19	12441008
Assessment of bioaccumulation, neuropathology, and neurobehavior following subchronic (90 days) inhalation in Sprague-Dawley rats exposed to manganese phosphate.	2002 Sep 1	12387753
Effects of N-ethylmaleimide on conformational equilibria in purified cardiac muscarinic receptors.	2002 Sep 27	12119286
Activation of cholinergic and adrenergic receptors increases the concentration of extracellular adenosine in the cerebral cortex of unanesthetized rat.	2003	12605898
Role of protein kinase C in central muscarinic inhibitory mechanisms regulating voiding in rats.	2003	12559102
Cannabinoid CB(1) receptor-mediated inhibition of hippocampal acetylcholine release is preserved in aged mice.	2003 Apr	12721097
Role of specific muscarinic receptor subtypes in cholinergic parasympathomimetic responses, in vivo phosphoinositide hydrolysis, and pilocarpine-induced seizure activity.	2003 Apr	12713643
Pharmacological discrimination between muscarinic receptor signal transduction cascades with bethanechol chloride.	2003 Apr	12711626
Characterization of muscarinic autoreceptors in the rabbit hippocampus and caudate nucleus.	2003 Apr	12675124
Comparison of the pharmacological antagonism of M2 and M3 muscarinic receptors expressed in isolation and in combination.	2003 Apr 15	12694864
Modulatory action of acetylcholine on striatal neurons: microiontophoretic study in awake, unrestrained rats.	2003 Feb	12581179
Activation of muscarinic m5 receptors inhibits recombinant KCNQ2/KCNQ3 K+ channels expressed in HEK293T cells.	2003 Feb 21	12591092
PMA decreases the proliferation of retinal cells in vitro: the involvement of acetylcholine and BDNF.	2003 Jan	12441170
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
Neurotransmitter release and its presynaptic modulation in the rat hippocampus after selective damage to cholinergic or/and serotonergic afferents.	2003 Jan 30	12507688
Characteristics of changes in cholinergic function and impairment of learning and memory-related behavior induced by olfactory bulbectomy.	2003 Jan 6	12493626
Cyclic ADP-ribose contributes to contraction and Ca2+ release by M1 muscarinic receptor activation in coronary arterial smooth muscle.	2003 Jan-Feb	12644723
Cholinergic regulation of pericyte-containing retinal microvessels.	2003 Jun	12560212
Bidirectional modulation of visual plasticity by cholinergic receptor subtypes in the frog optic tectum.	2003 Mar	12670313
Regulation of muscarinic acetylcholine receptor function in acetylcholinesterase knockout mice.	2003 Mar	12667913
The presence and functions of muscarinic receptors in human T cells: the involvement in IL-2 and IL-2 receptor system.	2003 Mar 28	12628467
A beta-induced TNF-alpha expression and acetylcholine action in mouse glial cells.	2003 Mar 28	12628466
Muscarinic receptor subtypes mediating central and peripheral antinociception studied with muscarinic receptor knockout mice: a review.	2003 Mar 28	12628455
Muscarinic receptor activation protects cells from apoptotic effects of DNA damage, oxidative stress, and mitochondrial inhibition.	2003 Mar 28	12538580
The effect of acetylcholinesterase-inhibition on depolarization-induced GABA release from rat striatal slices.	2003 Mar 3	12499118
The phospholipase C-IP3 pathway is involved in muscarinic antinociception.	2003 May	12736633
Presynaptic modulation of acetylcholine, noradrenaline, and serotonin release in the hippocampus of aged rats with various levels of memory impairments.	2003 May 15	12754090
Muscarinic acetylcholine receptor compounds alter net Ca2+ flux and contractility in an invertebrate smooth muscle.	2003 Nov	12687408

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:11:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:11:17 GMT 2023`
Record UNII	5RY0UWH1JL
Record Status	`Validated (UNII)`
Record Version

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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