Ayahuasca: alkaloids, plants & analogs
Section 1 :
Trivia about 1-Methyl-β-Carbolines found in Hoasca Brews
| Rf | Rf | Subl. | Fluorescence (under UV) | Chromophores (3) | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Y/N | Maxima (Agurell 1969) | ||||||||||
| Reference or Assay | a | b | 4 | 4 | 2 | 5 | D | E | NN | F | HC |
| Harmine | 0.64 | 0.73 | Yes | Yes | Royal Blue | Indigo-Blue (2) or Yellow-Green (3) | Orange | None | Dull Violet | Navy Blue | na |
| Harmaline | 0.07 | 0.38 | Yes | Yes | Whitish Blue | na | na | None (4) | na | na | na |
| Tetrahydroharmine | 0.13 | 0.66 | Yes | Yes | na | na | Orange | None (Yes) (5) | Dull Violet | Navy Blue | Purple |
References:
- Agurell et al. Acta Chemica Scandinavica. 23(3):903-916. 1969. [Maxima 355 mm (EtOH)].
- Der Marderosian et al. American Journal of Pharmacy. 140:137-147. 1968.
- Ghosal S, Mazumder UK, Bhattacharya SK. "Chemical and pharmacological evaluation of Banistereopsis argentea Spring ex Juss." Journal of Pharmaceutical Sciences. 60(8):1209-1212. 1971. (b)
- Hochstein and Paradies. Journal of the American Chemical Society 79: 5735-5736. 1952 (a)
- Marion p. 394. 1952. "The Indole Alkaloids." pp. 369-498 (Ch. 13) in: R.H.F. Manske & H.L. Holmes (eds.) The Alkaloids. Chemistry and Physiology. Vol. 2" Academic Press, New York.
Solvent systems:
- a. On Chloroform-Formamide system [Ref. 4: citing Hochstein et al. (1955) JACS 77: 3551.
- b. Ref. 3: Using Silica Gel G chromatoplates and Methyl alcohol-Chloroform-Acetic acid (75:25:15) as developer.
Assay Reagents:
- D: Dragendorff's
- E: Ehrlich's
- F: Fröhde
- HC: Hopkin-Cole
- NN: α-Nitroso-β-naphtholnitrous acid
Abbreviations:
- na : Not Available.
- Y/N : simple yes no answer
- Rf : standard value measurements used for TLC, a fractional expression of how far a band migrated relative to the distance the solvent migrated.
- Subl. : Sublimes, sublimates
Notes:
(1) Ghosal and coworkers (3.) reported that indole-3-alkylamines and tetrahydro-β-carbolines showed a light-blue fluorescence under UV on papers, aromatic β-carbolines showed violet and 3,4-dihydro-β-carbolines showed a sea-green fluorescence. (It must be noted that these colors are not necessarily the same on alumina and DMT does not fluoresce within the visible range of the spectrum -- it DOES fluoresce outside the range so is meaasurable.) McKenna et al. 1984a states that tetrahydro-β-carbolines (and DMT) are visible as dark spots under short wave UV while aromatic and dihydro-β-carbolines showed strong colors under longwave UV.
Banerjee & Ghosal found that crudely purified 5-MeO-DMT has a pale yellow fluorescence and 5-MeO-DMT-N-oxide has a dull red color (both under UV). Appleseed reported not seeing any fluorescence with 5-MeO-DMT (Personal communication; 1995)
(2) In Acidic solutions.
(3) In Basic solutions. The transition occurs within the pH interval 7.2-8.9, and can be used in quantitative estimations, according to Marion.
(4) According to McKenna et al. 1984a Journal of Ethnopharmacology 10 (2): 195-223.
(5) Also according to McKenna et al.1984a:
While there is no immediate reaction with Ehrlich's, THH, unlike harmine and harmaline, shows the slow development of robin's-egg blue over a 24 hour period. Tryptamines, on the other hand, react within 30 minutes; usually showing a dark blue or violet.