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 168 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Agonist 2752	5.48 null [pKi]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Agonist 2752	5.03 null [pKi]
Muscarinic acetylcholine receptor M3 160 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Agonist 2752	5.28 null [pKi]
Muscarinic acetylcholine receptor M4 87 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Agonist 2752	5.15 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Muscarinic acetylcholine receptor compounds alter net Ca2+ flux and contractility in an invertebrate smooth muscle.	2003-11	12687408
Cholinergic regulation of pericyte-containing retinal microvessels.	2003-06	12560212
Presynaptic modulation of acetylcholine, noradrenaline, and serotonin release in the hippocampus of aged rats with various levels of memory impairments.	2003-05-15	12754090
The phospholipase C-IP3 pathway is involved in muscarinic antinociception.	2003-05	12736633
Comparison of the pharmacological antagonism of M2 and M3 muscarinic receptors expressed in isolation and in combination.	2003-04-15	12694864
Cannabinoid CB(1) receptor-mediated inhibition of hippocampal acetylcholine release is preserved in aged mice.	2003-04	12721097
Role of specific muscarinic receptor subtypes in cholinergic parasympathomimetic responses, in vivo phosphoinositide hydrolysis, and pilocarpine-induced seizure activity.	2003-04	12713643
Pharmacological discrimination between muscarinic receptor signal transduction cascades with bethanechol chloride.	2003-04	12711626
Characterization of muscarinic autoreceptors in the rabbit hippocampus and caudate nucleus.	2003-04	12675124
The presence and functions of muscarinic receptors in human T cells: the involvement in IL-2 and IL-2 receptor system.	2003-03-28	12628467
A beta-induced TNF-alpha expression and acetylcholine action in mouse glial cells.	2003-03-28	12628466
Muscarinic receptor subtypes mediating central and peripheral antinociception studied with muscarinic receptor knockout mice: a review.	2003-03-28	12628455
Muscarinic receptor activation protects cells from apoptotic effects of DNA damage, oxidative stress, and mitochondrial inhibition.	2003-03-28	12538580
The effect of acetylcholinesterase-inhibition on depolarization-induced GABA release from rat striatal slices.	2003-03-03	12499118
Bidirectional modulation of visual plasticity by cholinergic receptor subtypes in the frog optic tectum.	2003-03	12670313
Regulation of muscarinic acetylcholine receptor function in acetylcholinesterase knockout mice.	2003-03	12667913
Activation of muscarinic m5 receptors inhibits recombinant KCNQ2/KCNQ3 K+ channels expressed in HEK293T cells.	2003-02-21	12591092
Modulatory action of acetylcholine on striatal neurons: microiontophoretic study in awake, unrestrained rats.	2003-02	12581179
Neurotransmitter release and its presynaptic modulation in the rat hippocampus after selective damage to cholinergic or/and serotonergic afferents.	2003-01-30	12507688
Role of muscarinic receptors in the activation of the ventral subiculum and the consequences for dopamine release in the nucleus accumbens.	2003-01-24	12559371
Characteristics of changes in cholinergic function and impairment of learning and memory-related behavior induced by olfactory bulbectomy.	2003-01-06	12493626
PMA decreases the proliferation of retinal cells in vitro: the involvement of acetylcholine and BDNF.	2003-01	12441170
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
Cholinergic modulation of basal and amphetamine-induced dopamine release in rat medial prefrontal cortex and nucleus accumbens.	2002-12-20	12468043
Evaluation of the central properties of several Hypericum species from the Canary Islands.	2002-12	12458477
The spinal antinociceptive effects of cholinergic drugs in rats: receptor subtype specificity in different nociceptive tests.	2002-11-19	12441008
Amygdala modulation of memory consolidation: interaction with other brain systems.	2002-11	12559833
Streptozotocin-induced diabetes impairs G-protein linked signal transduction in vascular smooth muscle.	2002-11	12487372
Evaluation of muscarinic agonist-induced analgesia in muscarinic acetylcholine receptor knockout mice.	2002-11	12391271
Effects of N-ethylmaleimide on conformational equilibria in purified cardiac muscarinic receptors.	2002-09-27	12119286
Muscarinic receptors of the neostriatum--their role in controlling operant behavior in dogs.	2002-09-24	12243260
Assessment of bioaccumulation, neuropathology, and neurobehavior following subchronic (90 days) inhalation in Sprague-Dawley rats exposed to manganese phosphate.	2002-09-01	12387753
Cholinergic activation of the basolateral amygdala regulates unlearned freezing behavior in rats.	2002-08-21	12191818
Validation of a new computerized system for recording and analysing drug-induced tremor in rats.	2002-08-17	12183189
Multiple muscarinic acetylcholine receptor subtypes modulate striatal dopamine release, as studied with M1-M5 muscarinic receptor knock-out mice.	2002-08-01	12151512
Activation of histaminergic H3 receptors in the rat basolateral amygdala improves expression of fear memory and enhances acetylcholine release.	2002-08	12193196
M1 muscarinic receptor signaling in mouse hippocampus and cortex.	2002-07-19	12106668
Monoaminergic and cholinergic stimulation of masculine sexual behavior in neonatally demasculinized male rats.	2002-07	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.	2002-07	12065743
Possible role of vasopressin in the thermoregulatory response to chlorpyrifos in the rat.	2002-06	12403052
Modulation by adenosine of both muscarinic M1-facilitation and M2-inhibition of [3H]-acetylcholine release from the rat motor nerve terminals.	2002-06	12081652
Modulation of ANP-C receptor signaling by endothelin-1 in A-10 smooth muscle cells.	2002-05-15	12054468
Phthalic acid amygdalopetal lesion of the nucleus basalis magnocellularis induces reversible memory deficits in rats.	2002-05	11991764
Intravenously administered oxotremorine and atropine, in doses known to affect pain threshold, affect the intraspinal release of acetylcholine in rats.	2002-04	12076312
Cyclic ADP-ribose contributes to contraction and Ca2+ release by M1 muscarinic receptor activation in coronary arterial smooth muscle.	2002-02-05	12644723
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
[Effect of tea polyphenols and tea pigments on inducing the activity of phase II detoxicating enzymes and on the chemoprevention of liver precancerous lesions].	2000-05-30	12725062
[Behavior pharmacology of maprotiline, a new antidepressant].	1975-11	1240830

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 `Mon Mar 31 17:49:28 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:28 GMT 2025`
Record UNII	5RY0UWH1JL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXOTREMORINE

Common Name

English

NSC-330497

Preferred Name

English

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

Systematic Name

English

OXOTREMORINE [MI]

Common Name

English

OXYTREMORINE

Common Name

English

Code System Code Type Description

FDA UNII

5RY0UWH1JL