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Details

Stereochemistry RACEMIC
Molecular Formula C20H32NO
Molecular Weight 302.4742
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
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 / 1
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
A controlled trial of anti-Parkinson drugs in drug-induced Parkinsonism.
1966 Jun
Drug-induced extrapyramidal symptoms: their incidence and treatment.
1967 Jan
Double-blind comparison of levodopa and procyclidine in parkinsonism, with illustrations of levodopa-induced movement disorders.
1970 Dec
Double-blind comparison of levodopa and procyclidine in parkinsonism, with illustrations of levodopa-induced movement disorders.
1970 Dec
Central role of solar information flow in pregenetic evolution.
1971 Jun
Parenteral long-acting phenothiazines.
1972 Mar 25
Letter: Delayed drug-induced dystonias.
1973 Oct 20
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule.
1978 Oct 7
Sleep disturbance associated with fluphenazine HCl: a case report.
1979 Jul
Fluphenazine enanthate and fluphenazine decanoate in the treatment of schizophrenic outpatients: extrapyramidal symptoms and therapeutic effect.
1982 Mar
Toxic neurological reaction to lithium/thioridazine.
1983 Apr 2
Neuroleptic malignant syndrome.
1983 Jun 18
Rapid cycling following antidepressant in an adolescent.
1990 May 15
Acute dystonia due to amitriptyline.
1992 May
Antipsychotic drug-induced dysphoria.
1996 Oct
Bilateral ulnar nerve paralysis: an unreported complication of drug-induced extrapyramidal rigidity.
1997 Jun
Anti-nicotinic properties of anticholinergic antiparkinson drugs.
1998 Nov
An extrapyramidal reaction to ondansetron.
1998 Oct
Effects of combinational prophylactics composed of physostigmine and procyclidine on soman-induced lethality, seizures and brain injuries.
2002 Jan
Self-reported parkinsonian symptoms in the EPIC-Norfolk cohort.
2005 Aug 24
Lack of association between prepulse inhibition and antisaccadic deficits in chronic schizophrenia: implications for identification of schizophrenia endophenotypes.
2005 May
Primary care use of antipsychotic drugs: an audit and intervention study.
2005 Nov 29
Efficacy of immediate and subsequent therapies against soman-induced seizures and lethality in rats.
2006 Feb
Abdominal pain with rigidity secondary to the anti-emetic drug metoclopramide.
2006 May
Pharmacological therapies against soman-induced seizures in rats 30 min following onset and anticonvulsant impact.
2006 Oct 24
An overview of the clinical use of ondansetron in preschool age children.
2007 Jun
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.
2007 Jun
Clozapine and co-prescribed psychotropics: a short report.
2008 Apr 25
Stuttering priapism--a review of the therapeutic options.
2008 Aug
Anticonvulsant efficacy of drugs with cholinergic and/or glutamatergic antagonism microinfused into area tempestas of rats exposed to soman.
2008 Feb
The present approaches to the development of prophylactic and therapeutic antidotes against nerve agents.
2008 Jun
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 Jun
Antiparkinson drugs used as prophylactics for nerve agents: studies of cognitive side effects in rats.
2008 Jun
Enhanced cholinergic-mediated increase in the pro-inflammatory cytokine IL-6 in irritable bowel syndrome: role of muscarinic receptors.
2008 Oct
Role of the central cholinergic system in the therapeutics of schizophrenia.
2008 Sep
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 Dec
Fatalities associated with clozapine-related constipation and bowel obstruction: a literature review and two case reports.
2009 Jul-Aug
Trends in the molecular pathogenesis and clinical therapeutics of common neurodegenerative disorders.
2009 Jun 3
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 Mar
Selective T-type calcium channel blockade alleviates hyperalgesia in ob/ob mice.
2009 Nov
Acute dystonic reactions in a lady presenting with repetitive involuntary muscle twitching: a case report.
2009 Nov 9
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment.
2010 Dec
Roles of perirhinal and posterior piriform cortices in control and generation of seizures: a microinfusion study in rats exposed to soman.
2010 Jan
The use of organotypic hippocampal slice cultures to evaluate protection by non-competitive NMDA receptor antagonists against excitotoxicity.
2010 Mar
Ethanol extract of Angelica gigas inhibits croton oil-induced inflammation by suppressing the cyclooxygenase - prostaglandin pathway.
2010 Mar
Behavioral side effects in rats treated with acetylcholinesterase inhibitors suggested used as prophylactics against nerve agents.
2010 May
Structured relaxation in the treatment of akathisia: case series.
2010 May 25
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Two medical therapies very effective shortly after high levels of soman poisoning in rats, but only one with universal utility.
2013 Dec 15
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 01:34:32 UTC 2023
Edited
by admin
on Sat Dec 16 01:34:32 UTC 2023
Record UNII
THH8Q65426
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRICYCLAMOL
Common 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
TRICYCLAMOL CATION
Common Name English
Code System Code Type Description
PUBCHEM
22514
Created by admin on Sat Dec 16 01:34:33 UTC 2023 , Edited by admin on Sat Dec 16 01:34:33 UTC 2023
PRIMARY
CHEBI
8448
Created by admin on Sat Dec 16 01:34:33 UTC 2023 , Edited by admin on Sat Dec 16 01:34:33 UTC 2023
PRIMARY
FDA UNII
THH8Q65426
Created by admin on Sat Dec 16 01:34:33 UTC 2023 , Edited by admin on Sat Dec 16 01:34:33 UTC 2023
PRIMARY
CAS
60-48-0
Created by admin on Sat Dec 16 01:34:33 UTC 2023 , Edited by admin on Sat Dec 16 01:34:33 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY