---

6-Methoxyharman was claimed in Naranjo 1967 to be orally active as a mild hallucinogen at 10 mg or above. It does not appear to be a controlled substance.

This substance and/or 6-MeO-1,2,3,4-tetrahydro-β-carboline are probably both formed naturally in the pineal gland although definitive confirmation of this appears to be lacking. The latter was claimed to have been isolated from bovine pineal and was proposed as a pineal produced neurotransmitter but the claim was later withdrawn due to the same worker's inability to reliably replicate their results.

It can also be formed from melatonin by refluxing it in xylene containing phosphorus pentoxide (P₂O₅). (The latter is an increasingly dificult to obtain material for many.)

Melatonin can be made from 5-methoxytryptamine by reacting it with acetic anhydride at 10° for 12 hours, diluting with water, making the solution alkaline, extracting with methylene chloride, drying it with a dessicant and removing the solvent under vacuum.

It is also readily available commercially.
   page 96 of Smith 1981

10-Methoxyharmalan
#5867 in Merck Ninth
4,9-dihydro-6-methoxy-1-methyl-#H-pyrido[3,4-b]indole
1-methyl-6-methoxy-3,4-dihydro-2-carboline
3,4-dihydromethoxyharman
C₁₃H₁₄N₂O
MW 214.26
C 72.87%, H 6.59%, N 13.08%, O 7.47%
Preparation from 5-methoxytryptamine Spath & Lederer 1930 Ber. 63: 2102
Petrova et al 1963 Zh. Obshch. Khim. 33: 1333 [1963 CA 59: 10149b]



Adrenoglomerulotropin
#160 in Merck Ninth
2,3,4,9-tetrahydro-6-methoxy-1-methyl-1H-pyrido[3,4-b]indole
aldosterone stimulating hormone
ASH
1-methyl-6-methoxy-1,2,3,4-tetrahydro-2-carboline
C₁₃H₁₆N₂O
MW 216.27
C 72.19%, H 7.46%, N 12.95%, O 7.40%
Reported to have been isolated from extracts of pineal gland tissue
Farrell 1960 Circulation 21: 1009
Farrell & McIsaac 1961 Arch. Biochem. Biophys. 94: 543
Synthesis from 5-methoxytryptamine and acetaldehyde
McIsaac 1961 Biochem. Biophys. Acta 52: 607
Meek et al 1964 Chem & Ind. 622
Crystals mp 150-151^o
UV_max (EtOH) 225, 280 nm (log e 4.34, 3.86)
(0.1N HCl): 220, 273 nm (log e 4.40, 3.86
Rf 0.90 in Butanol-Acetic acid-Water (4:1:5)
same in Propanol-Water (7:3)
Therapeutic category: hormone
Above from Merck



10-Methoxy-harmalan
1-Methyl-6-methoxy-4,9-dihydro-3H-pyrido[3,4-b]indole
Hallucinogen (cites McIsaac,WM, PA Khairallah & IH Page 1961 Science 134: 674) [Ed.: This begs to be questioned further.]
#347 in Usdin and Efron (1979)



Harman = 1-methyl-9H-pyrido[3,4-b]indole

Harmalan = 4,9-dihydro-1-methyl-3H-pyrido[3,4-b]indole

A marginally connected side note of interest to some:

The Phalaris alkaloid 6-methoxy-2-methyl-1,2,3,4-tetrahydro-β-carboline was reported as a rearrangement product of 5-methoxytryptamine-N-oxide by Ghosal & Mukherjee 1966 [J. Org. Chem 2284] but Shannon & Leyshon 1971 pointed out that their UV spectrum does not support that assertion.