We've Moved! Visit our NEW FORUM to join the latest discussions. This is an archive of our previous conversations...

You can find the login page for the old forum here.
Harmalas and other less-known β-Carbolines Workthread Options
#1 Posted : 6/25/2012 9:31:08 AM

DMT-Nexus member


Posts: 14191
Joined: 19-Feb-2008
Last visit: 23-Jun-2024
Location: Jungle
This first post will be expanded as more information is pooled in.

AKA Telepathine; 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole

Harmine chemical and physical properties

Pharmacology of harmine (Trout's notes on ayahuasca)

Reported natural sources (Trout's notes on ayahuasca)


(NIST Database)

Harmine N-Oxide
CAS: 57498-78-9
MW 228.50

Alkaloid isolated from Banisteriopsis caapi 0.0005% (by dry weight?) in stem & leaf. (Hashimoto & Kawanishi 1975 apud Trout's Notes on Ayahuasca)


Harmaline chemical and physical properties

Reported plant sources (Trout's notes on ayahuasca)

Pharmacology of harmaline (Trout's notes on ayahuasca)


(NIST Database)

AKA Leptoflorine; Tetrahydroharmine; 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

MW: 216.278940 g/mol

Trout's Notes on ayahuasca

It appears THH does NOT orally activate DMT (Bioassay experiment with pure THH).


Colorimetric reagent results

THH chemical and physical properties


(NIST database)

AKA: 1,2-Dimethyl-7-Methoxy-1,2,3,4-Tetrahydro-β-Carboline

Analysis: (Agurell et al 1969)

AKA 1-Methyl-Tetrahydro-β-Carboline; MTHBC

Plant sources:
Diplopterys cabrerana (Agurell et al 1968 ), Acacia mucronata and acuminata (Acacia analysis thread)


(NIST database)

AKA 2-Methyl-Tetrahydro-β-Carboline; 2-methyl-1,2,3,4-tetrahydro-beta-carboline

Natural sources: Found in Psychotria viridis and ayahuasca brew (McIlhenny et al 2009). Found in jungle spice/Mimosa hostilis, as well as different Acacias (Acacia analysis thread; Jungle Spice analysis thread). It has also been found in different Phalaris (Phalaris analysis thread; Gander et al, 1976). Also check the dedicated 2-MTHBC discussion thread for more info.


(NIST database)

AKA Nb-Methyltetrahydroharman; 1,2-Dimethyl-Tetrahydro-β-Carboline; 1,2-DMTHBC

AKA Harmane; 1-methyl-9H-pyrido[3,4-b]indole

Natural sources: Found in different food and tobacco smoke (Herraiz 2004). Found in different Passiflora spp (Rehwald et al 1995; Slaytor et al 1968; Passiflora thread). It has also been found in several other plants including the leaves of Uncaria attenuata ssp. attenuata, Uncaria orientalis, Uncaria canescens spp canescens (Phillipson and Hemingway 1975) and the roots of Strychnos usambarensis (Angenot et al 1975)

It's also an endogenous substance present in mammalian metabolism including humans (Robinson et al 2003)



Plant sources: Anadenanthera peregrina (Agurell et al 1969)

Analysis: (Agurell et al 1969)


Plant sources: Some Phalaris spp. (Festi and Samorini 1994)



(Agurell et al 1969)


Formed by picted-spengler ciclization on 5-MeO-NMT (Agurell et al 1969)

Plant sources: Anadenanthera peregrina (Agurell et al 1969); Some Phalaris spp. (Festi and Samorini 1994)

AKA 2,3,4,9-tetrahydro-6-methoxy-1H-Pyrido[3,4-b]indol-1-one

MW: 216
CAS#: 17952-87-3

Analysis: (NIST database)


CAS: 26579-69-1
Mass 216.2359; Exact mass 216.089877638
IUPAC name: 7-methoxy-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-one
Appearance: White needles from CHCl3 and MeOH
mp 197-198 °C (dec.)
MS: m/e 216 (100), 201 (23), 187 (35) and 159 (90). M+ found at 216.088, calc'd at 216.090.
UV λmax (MeOH): 249 (log ε 4.41) and 314 (4.29) nm
IR νmax (Nujol): 3100-3400, 1660, 1625: 1540, 1517, and 1513 cm^-1
1H NMR: δ 2.76-3.08 (2-H, m, H-3 or H-4), 3.39-3.73 (2-H, m, H-4 or H-3), 3.79 (3-H, s, OMe), 6.76 (1-H, q, J = 0.7 Hz; H-6), 6.92 (1-H, d, J = 2.1 Hz; H-Cool 7.51 (1-H, q, J = 8.8 Hz; H-5), 7.39 (1-H, b, lactamic NH), and 11.38 (1-H, b, indolic NH)
Present in Banisteriopsis caapi at 0.0005%.

Found in B. caapi at 0.0005%. (Hashimoto & Kawanashi 1976), found in significant quantity (14% of chemical content) in ourinhos analysis (B caapi analysis thread)

AKA: 6-Methoxy-Tetrahydro-β-Carboline

Analysis: (NIST database)

Natural sources: Pinoline is a part of human metabolism and is synthesized by the pineal gland

Others to add: harmalol, harmol, tryptoline, tetrahydronorharmine, harmic acid methylester, harmalinic acid, harmic amide, acetyl norharmine, norharman


Agurell, S. et al. (1968 ) American Journal of Pharmacy 140: 148-151. "Alkaloid Content of Banisteriopsis Rusbyana." [Stig Agurell, Bo Holmstedt & Jan-Erik Lindgren]

Agurell et al 1969. Alkaloids in certain species of Virola and other south american plants of ethnopharmacologic interest. Download link

Gander et al 1976 The occurrence of 2-methyl-1,2,3,4-tetrahydro-β-carboline and variation in alkaloids in Phalaris arundinacea. Phytochemistry. Volume 15, Issue 5, 1976, Pages 737–738. Download link

McIlhenny E. et al (2009) Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry" Journal of Chromatography A. Volume 1216, Issue 51, 18 December 2009, Pages 8960-8968 . Download link

Phillipson, J.D., Hemingway, S.R., 1975. Chromatographic and spectroscopic methods for the identification of alkaloids from herbarium samples of the genus Uncaria. J. Chromatography 105, 163–178.

Rehwald et al 1995 Trace analysis of harman alkaloids in passiflora incarnata by reversed-phase high performance liquid chromatography. Phytochemical Analysis Volume 6, Issue 2, pages 96–100, March/April 1995

Robinson et al 2003 Endogenous beta-carbolines as clonidine-displacing substances. Ann N Y Acad Sci. 2003 Dec;1009:157-66.Abstract link

Slaytor et al 1968. The biosynthesis and metabolism of harman in passiflora edulis—I : The biosynthesis of harman. Phytochemistry. Volume 7, Issue 4, April 1968, Pages 605–611

Trout's notes: Ayahuasca: alkaloids, plants & analogs. Online book

STS is a community for people interested in growing, preserving and researching botanical species, particularly those with remarkable therapeutic and/or psychoactive properties.
#2 Posted : 6/25/2012 9:56:58 AM

DMT-Nexus member

Posts: 2229
Joined: 22-Jul-2011
Last visit: 02-May-2024
Location: in the underbelly of the cosmic womb
kudos endlessness.. really getting the forums much tidier for recording data Smile
#3 Posted : 6/28/2012 12:59:26 AM
member for the trees

Acacia expert | Skills: Acacia, Botany, Tryptamines, CounsellingExtraordinary knowledge | Skills: Acacia, Botany, Tryptamines, CounsellingSenior Member | Skills: Acacia, Botany, Tryptamines, Counselling

Posts: 4003
Joined: 28-Jun-2011
Last visit: 27-May-2024
..much needed coordination of info, thank you endlessness..
#4 Posted : 7/5/2012 3:20:24 AM
member for the trees

Acacia expert | Skills: Acacia, Botany, Tryptamines, CounsellingExtraordinary knowledge | Skills: Acacia, Botany, Tryptamines, CounsellingSenior Member | Skills: Acacia, Botany, Tryptamines, Counselling

Posts: 4003
Joined: 28-Jun-2011
Last visit: 27-May-2024
..couple of detail additions to the above info so far, endlessness..

N-Methyl-Tetrahydroharman was the main alkaloid (0.3%) of Acacia complanata leaf, along with a little Tetrahydroharman..[Johns, Lamberton and Sioumis (1966)]..

Leptocladine was first found in Hammada leptoclada (Amaranthaceae) [Grazkuliev, I. K. et al. 1964]
#5 Posted : 4/28/2018 11:43:59 AM

DMT-Nexus member

Posts: 13
Joined: 31-Dec-2017
Last visit: 04-Aug-2019
I would love to ask you some questions can you pm me? https://www.dmt-nexus.me...m=877061&#post877061
#6 Posted : 4/28/2018 1:03:36 PM

dysfunctional word machine

Senior Member

Posts: 1831
Joined: 15-Mar-2014
Last visit: 11-Jun-2018
Location: at the center of my universe
2.22.222 wrote:
I would love to ask you some questions can you pm me? https://www.dmt-nexus.me...m=877061&#post877061

New forum members do not yet have PM privileges. Why not post your questions in the open? Others may also have valuable input.
Users browsing this forum

DMT-Nexus theme created by The Traveler
This page was generated in 0.105 seconds.