Pyrrobutamine

Title: Pyrrobutamine
CAS Registry Number: 91-82-7
CAS Name: 1-[4-(4-Chlorophenyl)-3-phenyl-2-butenyl]pyrrolidine
Additional Names: 1-[g-p-(chlorobenzyl)cinnamyl]pyrrolidine; 1-p-chlorophenyl-2-phenyl-4-pyrrolidyl-2-butene
Trademarks: Pyronil (Lilly)
Molecular Formula: C20H22ClN
Molecular Weight: 311.85
Percent Composition: C 77.03%, H 7.11%, Cl 11.37%, N 4.49%
Literature References: Prepn: J. Mills, US 2655509 (1953 to Eli Lilly). Pharmacology and toxicity: H. M. Lee et al., Proc. Soc. Exp. Biol. Med. 80, 458 (1952). Pharmacology and physical properties: N. G. Lordi, J. E. Christian, J. Am. Pharm. Assoc. 45, 300 (1956). Structure-activity and stereochemical study: A. F. Casy, R. R. Ison, J. Pharm. Pharmacol. 22, 270 (1970). GC-MS determn in urine: H. Maurer, K. Pfleger, J. Chromatogr. 430, 31 (1988).
Properties: Oily liquid, bp0.3 190-195°. On standing gives crystals, mp 48-49°. d25 1.1052. uv max (95% ethanol): 360, 243 nm (a 112, 9500), (c = 0.538, 0.00538 mg/ml).
Melting point: mp 48-49°
Boiling point: bp0.3 190-195°
Absorption maximum: uv max (95% ethanol): 360, 243 nm (a 112, 9500), (c = 0.538, 0.00538 mg/ml)
Density: d25 1.1052
Derivative Type: Diphosphate
CAS Registry Number: 135-31-9
Molecular Formula: C20H28ClNO8P2
Molecular Weight: 507.84
Percent Composition: C 47.30%, H 5.56%, Cl 6.98%, N 2.76%, O 25.20%, P 12.20%
Properties: Crystals from alcohol + ether, mp 129.5-130°. pKa1 8.77, pka2 5.23. Sol in warm water to the extent of 10%. Soly in alcohol at 25° about 5%. Soly at pH 7.4 (37.5°): 0.00087 M/l. Practically insol in chloroform, ether. LD50 in mice, guinea pigs (mg/kg): 1270 ±156, 1241 ±165 s.c.; 836.8 ±95, 625.6 ±41.9 i.m.; 1116 ±73, 992.6 ±107 orally; in mice (mg/kg): 53.53 ±1.61 i.v. (Lee).
Melting point: mp 129.5-130°
pKa: pKa1 8.77, pka2 5.23
Toxicity data: LD50 in mice, guinea pigs (mg/kg): 1270 ±156, 1241 ±165 s.c.; 836.8 ±95, 625.6 ±41.9 i.m.; 1116 ±73, 992.6 ±107 orally; in mice (mg/kg): 53.53 ±1.61 i.v. (Lee)
Derivative Type: Hydrochloride
Molecular Formula: C20H22ClN.HCl
Molecular Weight: 348.31
Percent Composition: C 68.97%, H 6.66%, Cl 20.36%, N 4.02%
Properties: Crystals from alcohol + ether, mp 227-228°.
Melting point: mp 227-228°
Derivative Type: Hydrobromide
Molecular Formula: C20H22ClN.HBr
Molecular Weight: 392.76
Percent Composition: C 61.16%, H 5.90%, Cl 9.03%, N 3.57%, Br 20.34%
Properties: Crystals from alcohol + ether, mp 228-229°.
Melting point: mp 228-229°
Therap-Cat: Antihistaminic.
Keywords: Antihistaminic; Alkylamine Derivatives.
Pyrrocaine Pyrrolidine Pyrrolnitrin Pyrrolysine Pyruvate Decarboxylase

Pyrrobutamine
Pyrrobutamine.png
Systematic (IUPAC) name
1-[(2E)-4-(4-chlorophenyl)-3-phenylbut-2-en-1-yl]pyrrolidine
Clinical data
Legal status  ?
Identifiers
CAS number 91-82-7
ATC code R06AX08
PubChem CID 5284614
ChemSpider 4447659
UNII VE6KP18S8X YesY
Chemical data
Formula C20H22ClN 
Mol. mass 311.848 g/mol
 YesY (what is this?)  (verify)

Pyrrobutamine is an antihistamine and anticholinergic.[1]