Harmaline → 10-Methoxyibogamine

反応式

[CH3:1][CH2:2][C@@H:3]1[C@@H:8]2[N:9]3[CH2:11][CH2:12][C:13]4[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=5[NH:15][C:14]=4[C@@H:7]2[CH2:6][C@@H:5]([CH2:10]3)[CH2:4]1.C1(C2NC3C(=CC=[C:31](C=3)[O:32]C)C=2CCN=1)C.COCC[C@@H]1[C@@H]2N3CCC4C5C=CC=CC=5NC=4[C@]2(C(OC)=O)CC(C3)C1.CC[C@@H]1[C@@H]2N3CCC4C5C=CC=CC=5NC=4[C@]2(C(OC)=O)C[C@@H](C3)C1>>[CH3:1][CH2:2][C@@H:3]1[C@@H:8]2[N:9]3[CH2:11][CH2:12][C:13]4[C:17]5[CH:18]=[C:19]([O:32][CH3:31])[CH:20]=[CH:21][C:16]=5[NH:15][C:14]=4[C@@H:7]2[CH2:6][C@@H:5]([CH2:10]3)[CH2:4]1

参加物

反応物 4

HCID 3564Harmaline

HCID 73489Coronaridine

HCID 442109(-)-Ibogamin2 回

HCID 46877888methyl (1S,17R,18S)-17-(2-methoxyethyl)-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

生成物 1

HCID 44210810-Methoxyibogamine

実験手順

Ibogamine (20-40 mg/kg), harmaline (10-40 mg/kg) and desethycoronaridine (10-40 mg/kg) were obviously tremorigenic for 3-4 h and no attempt was made to compare these drugs quantitatively. However, visual observations and videotape recordings of 18-methoxycoronaridine (40 mg/kg) and both R- and S-enantiomers of both ibogamine (40 mg/kg) and coronaridine (40 mg/kg) indicated very little if any tremorigenic activity. The effects of these latter drugs were therefore assessed using the automated testing procedure developed to quantitate tremors. Ibogains (40 mg/kg) and saline (1 ml/kg) were used as positive and negative controls, respectively. While ibogaine produced a significant increase in movements indicative of tremors, the 18-methoxycoronaridine and the ibogamine and coronaridine enantiomers had no effects that differed significantly from the effects of saline.