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Harmalas and other less-known β-Carbolines Workthread Options
 
endlessness
#1 Posted : 6/25/2012 9:31:08 AM

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This first post will be expanded as more information is pooled in.

Harmine
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)

Analysis:

(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


Harmaline chemical and physical properties

Reported plant sources (Trout's notes on ayahuasca)

Pharmacology of harmaline (Trout's notes on ayahuasca)

Analysis:

(NIST Database)


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


MW: 216.278940 g/mol

Pharmacology
Trout's Notes on ayahuasca

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

Chemistry

Colorimetric reagent results

THH chemical and physical properties

Analysis:

(NIST database)



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


Analysis: (Agurell et al 1969)








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


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

Analysis:

(NIST database)



2-MTHBC
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.

Analysis

(NIST database)


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







Harman
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)

Analysis:







1,2-dimethyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline



Plant sources: Anadenanthera peregrina (Agurell et al 1969)

Analysis: (Agurell et al 1969)







2,9-dimethyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline
AKA DMTHC



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








2-Methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline


Analysis:

(Agurell et al 1969)

Chemistry:

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)





6-Methoxy-Tetrahydro-1-Norharmanone
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)





Ketotetrahydronorharmine



CAS: 26579-69-1
C12H12N2O2
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)




Pinoline
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




References

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
 

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acacian
#2 Posted : 6/25/2012 9:56:58 AM

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kudos endlessness.. really getting the forums much tidier for recording data Smile
 
nen888
#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

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..much needed coordination of info, thank you endlessness..
 
nen888
#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

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..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]
.
 
2.22.222
#5 Posted : 4/28/2018 11:43:59 AM

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I would love to ask you some questions can you pm me? https://www.dmt-nexus.me...m=877061&#post877061
 
pitubo
#6 Posted : 4/28/2018 1:03:36 PM

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2.22.222 wrote:
I would love to ask you some questions can you pm me? https://www.dmt-nexus.me...=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.
 
 
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