Compound Selection

Formula: C12H10N2

MW: 182.22

CAS: 486-84-0



IUPAC: methylbeta-carboline

Smiles: c1ccc2c([nH]c3c2ccnc3C)c1

Harmane 98%, From Bark of Sickingia rubra




N+O: 2

Chiral Centers: 0

LogP: 3.18

LogS: -3.84


Monograph Number: 0004630

Title: Harman

CAS Registry Number: 486-84-0

CAS Name: 1-Methyl-9H-pyrido[3,4-b]indole

Additional Names: 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); Spath, 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.

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