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Details

Stereochemistry RACEMIC
Molecular Formula C20H32NO
Molecular Weight 302.4742
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of TRICYCLAMOL

SMILES

C[N+]3(CCC(O)(C1CCCCC1)C2=CC=CC=C2)CCCC3

InChI

InChIKey=FRBBPWXCRBHYJQ-UHFFFAOYSA-N
InChI=1S/C20H32NO/c1-21(15-8-9-16-21)17-14-20(22,18-10-4-2-5-11-18)19-12-6-3-7-13-19/h2,4-5,10-11,19,22H,3,6-9,12-17H2,1H3/q+1

HIDE SMILES / InChI

Molecular Formula C20H31NO
Molecular Weight 301.4662
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity ( + / - )

Tricyclamol is a quaternary ammonium compound, which is a crystalline odorless substance, readily soluble in water. It may be given by mouth or by subcutaneous injection. Tricyclamol was used for its spasmolytic action on smooth muscle. In animals it inhibits the spasmogenic effects of acetylcholine (ACh), carbachol, pilocarpine and barium chloride. In relaxing ACh-induced spasm of isolated rabbit ileum the activities of the dextro and laevo isomers of tricyclamol were approximately 0.006 and 2 times that of atropine sulphate respectively. Further, in inhibiting the stretch reflex of isolated guinea-pig ileum the laevo isomer was much more active than the dextro and about twice as potent as the racemate. Tricyclamol blocks the superior cervical ganglion. Tricyclamol chloride has a marked effect in reducing the motility of the stomach and duodenum, and to a far greater extent than the results produced by hyoscyamine. This action may be of value in controlling the pain of peptic ulceration, since it is likely that the pain, at least in part, is due to spasm.

Approval Year

PubMed

PubMed

TitleDatePubMed
Two medical therapies very effective shortly after high levels of soman poisoning in rats, but only one with universal utility.
2013-12-15
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011-07-14
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010-12
Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment.
2010-12
Structured relaxation in the treatment of akathisia: case series.
2010-05-25
Behavioral side effects in rats treated with acetylcholinesterase inhibitors suggested used as prophylactics against nerve agents.
2010-05
The use of organotypic hippocampal slice cultures to evaluate protection by non-competitive NMDA receptor antagonists against excitotoxicity.
2010-03
Ethanol extract of Angelica gigas inhibits croton oil-induced inflammation by suppressing the cyclooxygenase - prostaglandin pathway.
2010-03
Roles of perirhinal and posterior piriform cortices in control and generation of seizures: a microinfusion study in rats exposed to soman.
2010-01
Mechanisms of action of antipsychotic drugs of different classes, refractoriness to therapeutic effects of classical neuroleptics, and individual variation in sensitivity to their actions: Part II.
2009-12
Acute dystonic reactions in a lady presenting with repetitive involuntary muscle twitching: a case report.
2009-11-09
Selective T-type calcium channel blockade alleviates hyperalgesia in ob/ob mice.
2009-11
Fatalities associated with clozapine-related constipation and bowel obstruction: a literature review and two case reports.
2009-08-19
Trends in the molecular pathogenesis and clinical therapeutics of common neurodegenerative disorders.
2009-06-03
Physiological and pathological role of alpha-synuclein in Parkinson's disease through iron mediated oxidative stress; the role of a putative iron-responsive element.
2009-03
Enhanced cholinergic-mediated increase in the pro-inflammatory cytokine IL-6 in irritable bowel syndrome: role of muscarinic receptors.
2008-10
Role of the central cholinergic system in the therapeutics of schizophrenia.
2008-09
Stuttering priapism--a review of the therapeutic options.
2008-08
The present approaches to the development of prophylactic and therapeutic antidotes against nerve agents.
2008-06
Amisulpride plus valproate vs haloperidol plus valproate in the treatment of acute mania of bipolar I patients: a multicenter, open-label, randomized, comparative trial.
2008-06
Antiparkinson drugs used as prophylactics for nerve agents: studies of cognitive side effects in rats.
2008-06
Clozapine and co-prescribed psychotropics: a short report.
2008-04-25
Anticonvulsant efficacy of drugs with cholinergic and/or glutamatergic antagonism microinfused into area tempestas of rats exposed to soman.
2008-02
Low dose quetiapine induced galactorrhoea: a case report.
2007-07-24
Newer antipsychotics and the rabbit syndrome.
2007-06-11
An overview of the clinical use of ondansetron in preschool age children.
2007-06
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.
2007-06
Measurements with fluorescent probes in primary neural cultures; improved multiwell techniques.
2007-02-15
Effects of combinational prophylactics composed of physostigmine and procyclidine on soman-induced lethality, seizures and brain injuries.
2002-01
Anti-nicotinic properties of anticholinergic antiparkinson drugs.
1998-11
An extrapyramidal reaction to ondansetron.
1998-10
Bilateral ulnar nerve paralysis: an unreported complication of drug-induced extrapyramidal rigidity.
1997-06
Antipsychotic drug-induced dysphoria.
1996-10
Rapid cycling following antidepressant in an adolescent.
1990-05-15
Effects of mianserin in neuroleptic-induced parkinsonism.
1986
Neuroleptic malignant syndrome.
1983-06-18
Toxic neurological reaction to lithium/thioridazine.
1983-04-02
Fluphenazine enanthate and fluphenazine decanoate in the treatment of schizophrenic outpatients: extrapyramidal symptoms and therapeutic effect.
1982-03
Sleep disturbance associated with fluphenazine HCl: a case report.
1979-07
Ethopropazine and benztropine in neuroleptic-induced parkinsonism.
1979-03
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule.
1978-10-07
A comparison of piribedil, procyclidine and placebo in the control of phenothiazine-induced parkinsonism.
1977-06
Abnormal involuntary movements induced by anticholinergic therapy.
1974
Letter: Delayed drug-induced dystonias.
1973-10-20
Parenteral long-acting phenothiazines.
1972-03-25
Central role of solar information flow in pregenetic evolution.
1971-06
Double-blind comparison of levodopa and procyclidine in parkinsonism, with illustrations of levodopa-induced movement disorders.
1970-12
Double-blind comparison of levodopa and procyclidine in parkinsonism, with illustrations of levodopa-induced movement disorders.
1970-12
Drug-induced extrapyramidal symptoms: their incidence and treatment.
1967-01
A controlled trial of anti-Parkinson drugs in drug-induced Parkinsonism.
1966-06
Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 20:54:05 GMT 2025
Edited
by admin
on Mon Mar 31 20:54:05 GMT 2025
Record UNII
THH8Q65426
Record Status Validated (UNII)
Record Version
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Name Type Language
TRICYCLAMOL
Common Name English
TRICYCLAMOL CATION
Preferred Name English
TRICYCLAMOL ION
Common Name English
PYRROLIDINIUM, 1-(3-CYCLOHEXYL-3-HYDROXY-3-PHENYLPROPYL)-1-METHYL-
Systematic Name English
(±)-1-(3-CYCLOHEXYL-3-HYDROXY-3-PHENYLPROPYL)-1-METHYLPYRROLIDINIUM
Systematic Name English
Code System Code Type Description
PUBCHEM
22514
Created by admin on Mon Mar 31 20:54:05 GMT 2025 , Edited by admin on Mon Mar 31 20:54:05 GMT 2025
PRIMARY
CHEBI
8448
Created by admin on Mon Mar 31 20:54:05 GMT 2025 , Edited by admin on Mon Mar 31 20:54:05 GMT 2025
PRIMARY
FDA UNII
THH8Q65426
Created by admin on Mon Mar 31 20:54:05 GMT 2025 , Edited by admin on Mon Mar 31 20:54:05 GMT 2025
PRIMARY
CAS
60-48-0
Created by admin on Mon Mar 31 20:54:05 GMT 2025 , Edited by admin on Mon Mar 31 20:54:05 GMT 2025
PRIMARY
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ENANTIOMER -> RACEMATE
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ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY