The Syrian Rue plant (seeds, roots, etc) contain a variety of alkaloids, the most prominent of which are the harmala alkaloids: harmine, harmaline, and tetrahydroharmaline. According to Jonathan Ott, surveys done on the plant material have shown the B-carboline alkaloids range from 2-7% of the dry weight of the mature seeds with harmine making up the largest part of this.

1841 - German chemist H. Goebel first isolates and names harmaline in an extract from Peganum harmala.
1847 - German chemist J. Fritzsche first isolates and names harmine from P. harmala.
1901 - Fischer isolates and names harmalol from P. harmala.
1980 - Allen & Holmstedt publish the presence of harmol, ruine, dihydroruine, and tetrahydroharmine in P. harmala seeds.

TiHKAL Entries:

• Harmine
• Harmaline
• Tetrahydroharmine

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NAME :	Harmine
CHEMICAL NAME :	7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole
ALTERNATE CHEMICAL NAMES :	7-Methoxy-1-methylpyrido[3,4-b]indole
ALTERNATE CHEMICAL NAMES :	banisterine; yageine; telepathine; leucoharmine.
CAS#	442-51-3
CHEMICAL FORMULA	C13H12N2O
MOLECULAR WEIGHT	212.25
MELTING POINT	262° C (dec) - (Hydrochloride dihydrate crystals)
MELTING POINT	321° C (anhydrous) - (Hydrochloride dihydrate crystals)
SOLUBILITY	freely soluble in hot water
OTHER	Flouresces in solution
LD50	38 mg/kg i.v.(mice)
From the Merck Index 12th Edition

NAME :	Harmaline
CHEMICAL NAME :	4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole
ALTERNATE CHEMICAL NAMES :	1-methyl-7-methoxy-3,4-dihydro-.beta.-carboline O-methylharmalol
ALTERNATE CHEMICAL NAMES :	3,4-dihydroharmine; harmidine; harmalol methyl ether; O-methylharmalol
CAS#	304-21-2
CHEMICAL FORMULA	C13H14N2O
MOLECULAR WEIGHT	216.279
MELTING POINT	173-176° C (plates from methanol)
MELTING POINT	204-205° C (N-Acetylharmaline) - (needles)
SOLUBILITY	freely soluble in hot water
OTHER	Flouresces in solution
From the Merck Index 12th Edition

NAME :	Tetrahydroharmine
CHEMICAL NAME :	7-Methoxy-1,2,3,4-Tetrahydro-Harmine
ALTERNATE CHEMICAL NAMES :	Harman, 1,2,3,4-Tetrahydro-B-Carboline, 7-Methoxy-1-Methyl-1,2,3,4-Tetrahydro
ALTERNATE CHEMICAL NAMES :	7-Methoxy-1,2,3,4-Tetrahydroharman; 1,2,3,4-Tetrahydroharmine;
ALTERNATE CHEMICAL NAMES :	7-Methoxy-1-Methyl-1,2,3,4-Tetrahydro-B-Carboline; 7-Meo-Thh; leptaflorine
CHEMICAL FORMULA	C13H16N2O4P
MOLECULAR WEIGHT	216.279
MELTING POINT	232-234#176; C (TiHKAL)

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RELATED VAULTS
Ayahuasca (brew)
Syrian Rue
Banisteriopsis Caapi
Harmala Vault
MAOI Vault

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MERCK INDEX ENTRIES
4647. Harmine. 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole; banisterine; yageine; telepathine; leucoharmine.

C13H12N2O; mol wt 212.25. C 73.57%, H 5.70%, N 13.20%, O 7.54%. CNS stimulant isolated from seeds of Peganum harmala L., Zygophyllaceae: Gobel, Ann. 38, 363 (1841); Reinhard et al., Phytochemistry 7, 503 (1968); from Banisteria caapi Spruce, Malpighiaceae: Hochstein, Paradies, J. Am. Chem. Soc. 79, 5735 (1957); from Banisteriopsis inebrians Morton, Malpighiaceae: O'Connell, Lynn, J. Am. Pharm. Assoc. 42, 753 (1953). Structure: Manske et al., J. Chem. Soc. 1927, 1, 240. Synthesis: Spth, Lederer, Ber. 63B, 120 (1930); Akaboro, Saito, ibid. 2245; Hahn et al., Ber. 67B, 2031 (1934), Ann. 520, 107, 123 (1935), Ber. 71B, 2163, 2175 (1938); Harvey, Robson, J. Chem. Soc. 1938, 97. Metabolism: Slotkin, DiStefano, J. Pharmacol. Exp. Ther. 174, 456 (1970). Toxicity study: K. K. Chen et al., J. Pharmacol. Exp. Ther. 79, 127 (1943).

Slender, orthorhombic prisms from methanol, mp 261 deg (dec). Sublimes. pKa 7.70. uv max (methanol): 241, 301, 336 nm (log .epsilon. 4.61, 4.21, 3.69). Absorption and fluorescence spectra: O. S. Wolfbeis, E. Furlinger, Z. Physikal. Chem. 129, 171 (1982). Slightly sol in water, alcohol, chloroform, ether.

Hydrochloride dihydrate, crystals, mp 262 deg (dec), mp 321 deg when anhydrous. Sol in 40 parts water, freely sol in hot water. Aq solns have blue fluorescence. LD50 i.v. in mice: 38 mg/kg (Chen).

4644. Harmaline. D,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole; 1-methyl-7-methoxy-3,4-dihydro-.beta.-carboline; 3,4-dihydroharmine; harmidine; harmalol methyl ether; O-methylharmalol.

C13H14N2O; mol wt 214.27. C 72.87%, H 6.59%, N 13.07%, O 7.47%. CNS stimulant from seeds of Peganum harmala L., Zygophyllaceae: Goebel, Ann. 38, 363 (1841); from Banisteria caapi Spruce, Malpighiaceae: Hochstein, Paradies, J. Am. Chem. Soc. 79, 5735 (1957). Structure: Manske et al., J. Chem. Soc. 1927, 1. Synthesis: Spth, Lederer, Ber. 63, 120, 2102 (1930); Spenser, Can. J. Chem. 37, 1851 (1959). Identity with harmidine: Robinson, Chem. Ind. (London) 1965, 605. Pharmacology: Fuentes, Longo, Neuropharmacology 10, 15 (1971). Metabolism: Ho et al., Biochem. Pharmacol. 20, 1313 (1971). Review of structure and synthesis work: Hofmann, Sv. Farm. Tidskr. 75, 933 (1971), C.A. 76, 149609g (1972).

Orthorhombic bipyramidal prisms, tablets from methanol, rhombic octahedra from ethanol, mp 229-231 deg. Solns fluoresce blue. pK 4.2. uv max (methanol): 218, 260, 376 nm (log .epsilon. 4.27, 3.90, 4.02). Slightly sol in water, alcohol, ether; quite sol in hot alcohol, dil acids.

Hydrochloride dihydrate, slender, yellow needles, moderately sol in water, alcohol.

N-Acetylharmaline, needles, mp 204-205 deg.

References:

• Ott, J. Pharmacotheon, 1996. Page 205.
• Kutlu H, Amal H, 1967. "Turkiyede yetisen Peganum harmala L. uzerinde kimyasal arastirmalar" Istanbul Universitesi Eczacilik Fakultesi Mecmuasi 3: 133-147. (from Ott)
• Flattery D, Schwartz M. Hoama and Harmaline 1989.