Procyclidine hydrochloride | CAS#32381-60-5 | antispasmodic

MedKoo Cat#: 461121 | Name: Procyclidine hydrochloride

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Procyclidine hydrochloride is a synthetic antispasmodic compound of relatively low toxicity. It has been used in the treatment of parkinsonism and extrapyramidal dysfunction.

Chemical Structure

Procyclidine hydrochloride

CAS#32381-60-5

Theoretical Analysis

MedKoo Cat#: 461121

Name: Procyclidine hydrochloride

CAS#: 32381-60-5

Chemical Formula: C19H30ClNO

Exact Mass: 323.2016

Molecular Weight: 323.91

Elemental Analysis: C, 70.46; H, 9.34; Cl, 10.94; N, 4.32; O, 4.94

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

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Synonym

Procyclidine hydrochloride; (+-)-Procyclidine hydrochloride; racemate-Procyclidine hydrochloride;

IUPAC/Chemical Name

1-cyclohexyl-1-phenyl-3-(pyrrolidin-1-yl)propan-1-ol hydrochloride

InChi Key

ZFSPFXJSEHCTTR-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H29NO.ClH/c21-19(17-9-3-1-4-10-17,18-11-5-2-6-12-18)13-16-20-14-7-8-15-20;/h1,3-4,9-10,18,21H,2,5-8,11-16H2;1H

SMILES Code

OC(C1=CC=CC=C1)(C2CCCCC2)CCN3CCCC3.[H]Cl

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Procyclidine hydrochloride is a synthetic antispasmodic compound of relatively low toxicity.

In vitro activity:

TBD

In vivo activity:

The chimney test in mice revealed, that application of procyclidine at 10 mg/kg together with phenobarbital and valproate, and procyclidine at 20 mg/kg with diazepam resulted in motor impairment. However, when procyclidine was applied at 10 mg/kg together with carbamazepine or diphenylhydantoin, no motor impairment was noted. The combined treatment of procyclidine (10 mg/kg) with carbamazepine, diphenylhydantoin, phenobarbital or valproate, as well as procyclidine (20 mg/kg) with diazepam caused significant worsening of long-term memory. Reference: J Neural Transm Gen Sect. 1994;97(1):1-12. https://pubmed.ncbi.nlm.nih.gov/7888145/

Preparing Stock Solutions

The following data is based on the product molecular weight 323.91 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

Zarnowski T, Kleinrok Z, Turski WA, Czuczwar SJ. The NMDA antagonist procyclidine, but not ifenprodil, enhances the protective efficacy of common antiepileptics against maximal electroshock-induced seizures in mice. J Neural Transm Gen Sect. 1994;97(1):1-12. doi: 10.1007/BF01277958. PMID: 7888145.

In vitro protocol:

TBD

In vivo protocol:

1: Myhrer T, Mariussen E, Enger S, Aas P. Capacities of metabotropic glutamate modulators in counteracting soman-induced seizures in rats. Eur J Pharmacol. 2013 Oct 15;718(1-3):253-60. doi: 10.1016/j.ejphar.2013.08.024. Epub 2013 Sep 7. PubMed PMID: 24021536. 2: Schjelderup L, Harbitz O, Groth P, Aasen AJ. Syntheses of (S)-(+)-trihexyphenidyl hydrochloride and (S)-(+)-procyclidine hydrochloride, two anticholinergics, using (S)-(-)-3-cyclohexyl-3-hydroxy-3-phenylpropanoic acid as chiral synthon. Acta Chem Scand B. 1987 May;41(5):356-61. PubMed PMID: 3673449. 3: Cho Y, Kim WS, Hur GH, Ha YC. Minimum effective drug concentrations of a transdermal patch system containing procyclidine and physostigmine for prophylaxis against soman poisoning in rhesus monkeys. Environ Toxicol Pharmacol. 2012 Jan;33(1):1-8. doi: 10.1016/j.etap.2011.10.002. Epub 2011 Oct 17. PubMed PMID: 22051905. 4: Campbell MJ, Demetriou B, Jones R. Assay of procyclidine hydrochloride, cyclizine hydrochloride and diethylcarbamazine citrate in tablets using ion-responsive electrodes. Analyst. 1980 Jun;105(1251):605-11. PubMed PMID: 7416480. 5: Vas CJ, Exley KA, Parsonage MJ. EEG activation by procyclidine hydrochloride in temporal lobe epilepsy. Electroencephalogr Clin Neurophysiol. 1967 Apr;22(4):395. PubMed PMID: 4164765. 6: Myhrer T, Aas P. Choice of approaches in developing novel medical countermeasures for nerve agent poisoning. Neurotoxicology. 2014 Sep;44:27-38. doi: 10.1016/j.neuro.2014.04.011. Epub 2014 May 9. Review. PubMed PMID: 24820435. 7: Camerman N, Camerman A. The stereochemical basis of anticonvulsant drug action. 3. The structure of procyclidine hydrochloride. Mol Pharmacol. 1971 Jul;7(4):406-12. PubMed PMID: 5113235. 8: Myhrer T, Enger S, Mariussen E, Aas P. Two medical therapies very effective shortly after high levels of soman poisoning in rats, but only one with universal utility. Toxicology. 2013 Dec 15;314(2-3):221-8. doi: 10.1016/j.tox.2013.08.005. Epub 2013 Aug 16. PubMed PMID: 23959147. 9: RENZI AA, MILCH LJ. Effectiveness of procyclidine hydrochloride (kemadrin) and cycrimine hydrochloride (pagitane) in the prevention of airsickness. J Aviat Med. 1958 Aug;29(8):587-9. PubMed PMID: 13575361. 10: Vas CJ, Exley KA, Parsonage MJ. Activation of the EEG by procyclidine hydrochloride in temporal lobe epilepsy. Epilepsia. 1967 Dec;8(4):241-51. PubMed PMID: 5238716. 11: Jang EJ, Lee YJ, Chung SJ, Shim CK. Nasal absorption of procyclidine in rats and dogs. Arch Pharm Res. 2001 Jun;24(3):219-23. PubMed PMID: 11440081. 12: El-Haj B, Al-Amri A, Ali HS. Target urinary analytes for the gas chromatographic- mass spectrometric detection of procyclidine and benzhexol in drug abuse cases. J Anal Toxicol. 2011 Mar;35(2):92-8. PubMed PMID: 21396228. 13: Sharma T, Galea A, Zachariah E, Das M, Taylor D, Ruprah M, Kumari V. Effects of 10 mg and 15 mg oral procyclidine on critical flicker fusion threshold and cardiac functioning in healthy human subjects. J Psychopharmacol. 2002 Jun;16(2):183-7. Erratum in: J Psychopharmacol. 2003 Mar;17(1):following table of contents. PubMed PMID: 12095079. 14: Rifkin A, Quitkin F, Kane J, Struve F, Klein DF. Are prophylactic antiparkinson drugs necessary? A controlled study of procyclidine withdrawal. Arch Gen Psychiatry. 1978 Apr;35(4):483-9. PubMed PMID: 215095. 15: Haug KH, Myhrer T, Fonnum F. The combination of donepezil and procyclidine protects against soman-induced seizures in rats. Toxicol Appl Pharmacol. 2007 Apr 15;220(2):156-63. Epub 2007 Jan 3. PubMed PMID: 17289099. 16: Choi EK, Park D, Yon JM, Hur GH, Ha YC, Che JH, Kim J, Shin S, Jang JY, Hwang SY, Seong YH, Kim DJ, Kim JC, Kim YB. Protection by sustained release of physostigmine and procyclidine of soman poisoning in rats. Eur J Pharmacol. 2004 Nov 28;505(1-3):83-91. PubMed PMID: 15556140. 17: GROSS H, LANGNER E. [Prophylaxis and therapy of a drug-related Parkinson syndrome with procyclidine hydrochloride (Kemadrin)]. Wien Klin Wochenschr. 1962 Aug 31;74:569-70. German. PubMed PMID: 13902214. 18: Kim WS, Cho Y, Kim JC, Huang ZZ, Park SH, Choi EK, Shin S, Nam SY, Kang JK, Hwang SY, Kim YB. Protection by a transdermal patch containing physostigmine and procyclidine of soman poisoning in dogs. Eur J Pharmacol. 2005 Nov 21;525(1-3):135-42. Epub 2005 Oct 27. PubMed PMID: 16256978. 19: Myhrer T, Enger S, Aas P. Behavioral side effects of prophylactic therapies against soman-induced seizures and lethality in rats. Toxicol Rep. 2014 May 14;1:102-113. doi: 10.1016/j.toxrep.2014.04.004. eCollection 2014. PubMed PMID: 28962231; PubMed Central PMCID: PMC5598500. 20: ZIER A, DOSHAY LJ. Procyclidine hydrochloride (kemadrin) treatment of parkinsonism; result in 108 patients. Neurology. 1957 Jul;7(7):485-9. PubMed PMID: 13451881.