Title: Harman
CAS Registry Number: 486-84-0
CAS Name: 1-Methyl-9
H-pyrido[3,4-
b]indole
Synonyms: 3-methyl-4-carboline; 2-methyl-b-carboline; aribine; loturine; passiflorin
Molecular Formula: C12H10N2
Molecular Weight: 182.22
Percent Composition: C 79.10%, H 5.53%, N 15.37%
Literature References: From bark of
Sickingia rubra (Mart.) K. Schum.
(Arariba rubra Mart.),
Rubiaceae; Symplocus racemosa Roxb.,
Symplocaceae; and
Passiflora incarnata L.,
Passifloraceae: Rieth, Wohler,
Ann. 120, 247 (1861); Sp?th,
Monatsh. Chem. 40, 351;
41, 401 (1920); Neu,
Arzneim.-Forsch. 4, 601 (1954). Structure: Neu,
ibid. 6, 94 (1956). Synthesis: Harvey, Robson,
J. Chem. Soc. 1938, 97; Snyder
et al., J. Am. Chem. Soc. 70, 222 (1948); Clemo, Holt,
J. Chem. Soc. 1953, 1313; Kametani
et al., ibid. (C) 1968, 1006. Isoln from cigarette smoke: Poindexter, Carpenter,
Chem. Ind. (London) 1962, 176. Toxicity study: E. B. Sigg
et al., Arch. Int. Pharmacodyn. 149, 164 (1964).
Properties: Bitter orthorhombic crystals from heptane + cyclohexane, mp 237-238°. Exhibits bright blue fluorescence in uv light. pKa: 7.37, 14.6. uv max (methanol): 234, 287, 347 nm (log e 4.57, 4.21, 3.66). Absorption and fluorescence spectra: O. S. Wolfbeis
et al., Monatsh. Chem. 113, 509 (1982). Practically insol in water. Sol in dil acids. LD50 i.p. in mice: 50 mg/kg (Sigg).
Melting point: mp 237-238°
pKa: pKa: 7.37, 14.6
Absorption maximum: uv max (methanol): 234, 287, 347 nm (log e 4.57, 4.21, 3.66)
Toxicity data: LD50 i.p. in mice: 50 mg/kg (Sigg)
Derivative Type: Hydrochloride
Molecular Formula: C12H10N2.HCl
Molecular Weight: 218.68
Percent Composition: C 65.91%, H 5.07%, N 12.81%, Cl 16.21%
Properties: Rosettes of needles from ethanol + 20% HCl in water, sublimes at 120-130°.