Procyclidine

Base Information

• Chemical Name: Procyclidine
• CAS No.: 77-37-2
• Deprecated CAS: 56172-67-9,107661-03-0
• Molecular Formula: C19H29 N O
• Molecular Weight: 287.445
• European Community (EC) Number: 201-023-0
• NSC Number: 169103
• UNII: C6QE1Q1TKR
• DSSTox Substance ID: DTXSID2023515
• Nikkaji Number: J4.199H
• Wikipedia: Procyclidine
• Wikidata: Q268997
• NCI Thesaurus Code: C73270
• Pharos Ligand ID: 9PWV7V52BT84
• Metabolomics Workbench ID: 42752
• ChEMBL ID: CHEMBL86715
• Mol file: 77-37-2.mol

Synonyms:Arpicolin;Hydrochloride, Procyclidine;Kemadren;Kemadrin;Mucinil;Osnervan;Procyclid;Procyclidine;Procyclidine Hydrochloride;Tricyclamol

Chemical Property of Procyclidine

Chemical Property:

• Melting Point: 85.5-86.5°
• Refractive Index: 1.5180 (estimate)
• Boiling Point: 433.5 °C at 760 mmHg
• Flash Point: 205.7 °C
• PSA: 23.47000
• Density: 1.057 g/cm³
• LogP: 3.87830
• Water Solubility.: 1.055mg/L(22.5 oC)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 287.224914549
• Heavy Atom Count: 21
• Complexity: 301

Purity/Quality:

99.0% ^*data from raw suppliers

PROCYCLIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C(CCN2CCCC2)(C3=CC=CC=C3)O
• Uses: Antiparkinsonian; relaxant (skeletal muscle).

Technology Process of Procyclidine

There total 5 articles about Procyclidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Pyrrinol (6072-22-6) → procyclidine (77-37-2)

Guidance literature:

With acetic acid; platinum; Hydrogenation;

Reference yield:

ethyl 3-tetrahydro-1H-1-pyrrolilpropanoate (6317-35-7) → procyclidine (77-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: platinum; aqueous acetic acid / Hydrogenation

With diethyl ether; acetic acid; platinum;

Reference yield:

phenylmagnesium bromide → procyclidine (77-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: platinum; aqueous acetic acid / Hydrogenation

With diethyl ether; acetic acid; platinum;

upstream raw materials:

1-phenyl-3-(pyrrolidin-1-yl)propan-1-one

cyclohexylmagnesium bromide

Pyrrinol

ethyl 3-tetrahydro-1H-1-pyrrolilpropanoate

Downstream raw materials:

(+/-)-1-ethyl-1-(3-cyclohexyl-3-hydroxy-3-phenyl-propyl)-pyrrolidinium; iodide

(+/-)-1-(3-cyclohexyl-3-hydroxy-3-phenyl-propyl)-1-methyl-pyrrolidinium; iodide

(S)-Procyclidine

(R)-Procyclidine

Refernces

Carbon-13 chemical shifts of three oxo-, six monohydroxy-, and six dihydroxycyclohexyl derivatives of procyclidine

10.1002/bscb.19820910708

The research aimed to elucidate the metabolic pattern of procyclidine, an anticholinergic drug used in the treatment of Parkinson's disease, by synthesizing and analyzing various derivatives of procyclidine, including dehydro-, monohydroxy-, oxo-, and dihydroxycyclohexyl derivatives. The study employed 13C-NMR spectroscopy to identify and characterize these derivatives, which were synthesized through a series of chemical reactions involving compounds such as 1,2,3,6-tetrahydrobenzaldehyde, 3-cyclohexenyl methyl ketone, and 1-(3-cyclohexenyl)-3-(1-pyrrolidinyl)-1-propanone. The researchers observed that the major metabolic pathways in rats involved mono- and dihydroxylation as well as ketone formation on the cyclohexyl part of the molecule. The conclusions were drawn by comparing the measured and calculated 13C chemical shifts of the synthesized derivatives, which helped in identifying the isolated metabolites. The study provided insights into the metabolic pathways of procyclidine and confirmed the structure of several metabolites through experimental and calculated chemical shifts.

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