I just has a view at the scifinder. The compounds with one additional -CH2- netween the nitrogen and the methyl group that branches the chain are reported to be very effective musclerelaxants. Here are some refs.:
Synthesis of muscle relaxant 4'-ethyl-2-methyl-3- pyrrolidinopropiophenone hydrochloride. Meng, Zhaoli; Zhao, Yanwei; Xi, Yanwei. Dep. Pharm., Shandong Med. Univ., Jinan, Peop. Rep. China. Zhongguo Yiyao Gongye Zazhi (1990), 21(11), 483-4. CODEN: ZYGZEA ISSN: 1001-8255. Journal written in Chinese. CAN 115:8469 AN 1991:408469 CAPLUS
Abstract
Propionylation of ethylbenzene with EtCOCl and AlCl3 gave 87% p-ethylpropiophenone, Mannich reaction of which with pyrrolidine and 36% CH2O soln. gave, after treatment with concd. HCl, 50% the title compd. (I).
Centrally acting muscle relaxant activities of 2-methyl-3- pyrrolidinopropiophenone derivatives. Yamazaki, Mitsuo; Aoki, Yasuji; Kato, Hideo; Ito, Yasuo; Kontani, Hitoshi; Koshiura, Ryozo. Res. Lab., Hokuriku, Seiyaku Co., Ltd., Katsuyama, Japan. Yakugaku Zasshi (1987), 107(9), 705-10. CODEN: YKKZAJ ISSN: 0031-6903. Journal written in Japanese. CAN 108:15785 AN 1988:15785 CAPLUS
Abstract
[2-Methyl-3-pyrrolidinopropiophenone derivs. I (R = H, alkyl, cyclohexyl, or fluoromethyl) were studied after oral or intraduodenal administration for centrally acting muscle-relaxant activity. Using the rotating rod method in mice, the Et, n-Pr, iso-Pr and n-Bu derivs. had equipotent activity, but when tested against decerebrate rigidity in rats, the Et deriv. was the most potent. The muscle relaxant activities of the cyclohexyl and fluoromethyl derivs. were weaker than that of other derivs. The hexobarbital-induced sleeping time was most prolonged by the compds. where R = H or n-Bu. The toxicity of I was increased when the length of the alkyl chain was increased. I had a greater inhibitory effect against nicotine-induced convulsion than did piperidinopropiophenone derivs.
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