Ayahuasca: alkaloids, plants & analogs
Section 3 : Part 2 :
A look at the MYRISTICACEAE
Previously published in 1995 as Trout's Notes on the Myristicaceae
Gymnacranthera paniculatum (A. DC) Warb.
1,5-dimethyl-gramine
(with 2-methyl-1,2,3,4-tetrahydro-β-carboline)
- Johns et al. 1967
Compsoneura ulei
[Schultes & Rodrigues #26116; Origin: Manáos, Brazil] Leaves assayed negative with Dragendorff and Ehrlich reagents
- Holmstedt et al. 1980
Dialyanthera otoba (H. et B. ) Warburg
Seed oil said to be employed by Colombian peasants to treat skin infections of domestic animals.
- Schultes & Holmstedt 1971
Dialyanthera parvifolia Markgraf
Vernacular name in eastern Peru is cumala roja.
Witoto Indians call it u-ku-na a; a name commonly applied in the same region to one or more species of Virola
- Schultes & Holmstedt 1971
Iryanthera crassifolia A. C. Smith
Bark decoction of this and a Piper species are used by Kubayarí Indians living near the base of Cerro Isibukuri in the Rio Kananarí for washing wounds.
Native to Amazonian Peru and Brazil as well as parts of Columbia (Comisaría del Vaupés)
- Schultes & Holmstedt 1971
Iryanthera coriacea
[Schultes & Rodrigues #26114; Origin: Manáos, Brazil] Leaves assayed negative with Dragendorff and Ehrlich reagents.
Bark assayed negative with Dragendorff and Ehrlich reagents.
Twigs assayed negative with Dragendorff and Ehrlich reagents.
- Holmstedt et al. 1980
Iryanthera grandis Ducke
Native to central Amazon of Brazil in the Madeira and Tapajoz basins
Also from Departamento de Loreto, Peru where its common name is cumala blanca a name also used in that area for Iryantha lanceolata and Osteophloem platyspermum.
Its Brazilian name is ucu-uba vermelha.
- Schultes & Holmstedt 1971
Iryanthera juruensis Warburg
Species widespread in Orinoco drainage area of Columbia and rather extensively on the Pacific coast.
Called mamita in the Llanos of San Martin
Called cuangare on the Pacific coast
Called ucuuba-rana in Brazil (Used, as are many related species, for seed oil)
Field test for alkaloids proved negative (Schultes, Raffauf & Soejarto #24105)
- Schultes & Holmstedt 1971
Iryanthera ulei Warburg
[Plowman, Schultes & Tovar #6919; Origin: Pebas, Peru (Alpha-Helix 1977)] 0.013 mg. of 5-methoxy-DMT in 100 grams of bark
- Holmstedt et al. 1980
Osteophloem platyspermum (A. DC.) Warb.
[DMK-78] N-methyl-l-tryptophan in leaves
- McKenna et al. (1984)
[Plowman, Schultes & Tovar #7095; Origin: Pebas, Peru (Alpha-Helix 1977)]
Bark assayed negative with Dragendorff and Ehrlich reagents
- Holmstedt et al. 1980
[Schultes & Rodriguez #26126; Origin: Manáos, Brazil]
0.62 mg of alkaloids in 100 grams of bark:
DMT
5-MeO-DMT
Bufotenine
- Holmstedt et al. 1980
[Prance #11117; Origin: Rio Mucajaí, Brazil]
Leaves assayed negative with Dragendorff and Ehrlich reagents
- Holmstedt et al. 1980
Found in Colombia (Comisaría del Vaupés and Comisaría del Putumayo) and Peru (Departmento de Loreto)
"...a not uncommon element of the flora of Amazonium Colombia."
Cumala blanca reported to be vernacular name. (Name also apllied to several Iryanthera spp.)
- Schultes & Holmstedt 1971
Virola sp.
[Schultes & Rodrigues #24603; Origin: Manáos, Brazil] Leaves, bark and twigs mixed together in can containing alcohol.
0.22 mg. of DMT in 100gm. of plant material.
- Holmstedt et al. 1980
Virola n. sp.(?)
[Schultes #26127] 0.07 mg. of DMT in 100 gm. of leaves.
- Holmstedt et al. 1980
Virola sp.
[Schultes #26130] Leaves and twigs assayed negative with Dragendorff and Ehrlich Reagents.
Materials mixed together in can containing alcohol.
- Holmstedt et al.
" This southeastern Brazilian species, has according to Teixeira de Fonseca, E. :
"Indicador de madeiras e plantas uteis do Brasil" (1922) 343), many folk uses. Because some of the uses are very similar to those of other species, especially those from the Amazon, it may be of interest to enumerate them. (See Kistler, L.L.: "Folk uses of the
Myristicacea" Term paper, ined., in Biology 207, Harvard University (1970) 35-36)
The seeds of Virola Bicahyba yield a fat employed to treat rheumatism, asthma, tumours of the joints, intestinal worms, skin diseases, erysipelas, hemorrhoids, and bad breathe. The kino is utilized as a styptic to treat bleeding breasts, colic, ulcerating sores
and wounds and for staunching many kinds of bleeding . it is reported to be a "brain stimulant", reviving the memory and the intelligence. Texeira further states that the seeds"...possesses, also, the properties of a narcotic." "
- Schultes & Holmstedt 1971
Note: this is one of the few references specifically about seeds being active. Perhaps worth exploring further in other species of Virola and other members of the Myristicaceae. Ed.
Virola calophylla Warb.
[Schultes #24603; Origin: Manáus, Brazil] 9 mg. of alkaloid / 100 gm. of dry bark:
91% N,N-dimethyltryptamine
9% 5-methoxy-N,N-dimethyltryptamine
1 mg. of alkaloid / 100 gm. of dry roots:
87% N,N-dimethyltryptamine
13% 5-methoxy-N,N-dimethyltryptamine
193 mg. of alkaloid / 100 gm. of dry flowers & shoots:
96% N,N-dimethyltryptamine
4% N-methyltryptamine
155 mg. of alkaloid / 100 gm. of dry leaves:
96% N,N-dimethyltryptamine
4% N-methyltryptamine
- Agurell et al. 1969
[Prance #14947; Origin: Rio Cuieras, Brazil]
9 mg. of alkaloid / 100 gm. of bark:
N,N-dimethyltryptamine
5-methoxy-N,N-dimethyltryptamine
1 mg. of alkaloid / 100 gm. of roots:
N,N-dimethyltryptamine
5-methoxy-N,N-dimethyltryptamine
115 mg. of alkaloid / 100 gm. of leaves:
N-methyltryptamine
N,N-dimethyltryptamine
- Holmstedt et al. 1980
Virola calophylloidea Markgrat
[Plowman, Schultes & Tovar #7093; Origin: Pebas, Peru (Alpha-Helix 1977)] 7.5 mg. per 100 grams of Bark:
50% DMT
45% 5-MeO-DMT
5% 5-MeO-MMT
- Holmstedt et al. 1980
[Prance #14312; Origin: Rio Curuquette, Brazil]
1.35 mg. per 100 grams of leaves:
100% DMT
- Holmstedt et al. 1980
[Prance #14954; Origin: Rio Cuieras, Brazil]
98 mg. per 100 grams of leaves:
100% DMT
- Holmstedt et al. 1980
Virola carinata (Spruce ex Bentham)
[Schultes & Rodrigues #26181a; Origin: Manáos, Brazil] 0.04 mg. per 100 grams of leaves,bark and twigs:
(Materials mixed in a can containing alcohol)
100% DMT
Holmstedt et al. 1980
Virola cuspidata (Benth) Warb.
[Prance #13994; Origin: Rio Ituxi, Brazil] Leaves assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
[Prance #13994; Origin: Rio Ituxi, Brazil]
Leaves assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
Otobaene, Hydroxyotobain and 3,4',5-Trimethoxy-trans-stilbene
- Blair et al. 1969
6-methoxytetrahydroharman (major)
6-methoxyharman (minor)
6-methoxyharmalan (minor)
and one unidentified component.
Also found that refluxing of 6-methoxytetrahydroharman in water for 8 hours and concentrating resulted in partial conversion to 6-methoxyharman and 6-methoxyharmalan
- Cassady et al. 1971
Virola cuspidata (Benth)Warb. sensu Ducke
500 gm. of leaves and stems gave 0.42 gm ofcrude basic fraction (0.08%)
250 mg. of basic fraction was enriched on Woelm neutral alumina and gave 76 mg. of fraction enriched in major component.
6-methoxytetrahydroharman (major) (13 mg. purified from the 76 mg. by TLC)
(one unidentified major and two unidentified minor alkaloids also present)
Results presented at a 1969 symposium published in 1972.
- Cassady et al. 1972 in Mothes (ed) pp.95-99
Virola divergens Ducke
[Schultes & Rodrigues _____; Origin: Manáos, Brazil] 0.5 mg. per 100 grams of leaves and bark : (Materials mixed in a can containing alcohol)
100% DMT
- Holmstedt et al. 1980
Virola elongata
[Plowman, Schultes & Tovar #6595; Origin: Pebas, Peru (Alpha-Helix 1977)] Leaves assayed negative with Dragendorff and Ehrlich Reagents.
Bark assayed negative with Dragendorff and Ehrlich Reagents.
Stem assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
[Plowman, Schultes & Tovar #6920; Origin: Pebas, Peru (Alpha-Helix 1977)]
Phloem:
tryptamine
N,N-dimethyltryptamine
N-methyltryptamine
2-methyl-1,2,3,4-tetrahydro-β-carboline
5-MeO-DMT
5-MeO-MMT
"Resin":
tryptamine
N,N-dimethyltryptamine
N-methyltryptamine
2-methyl-1,2,3,4-tetrahydro-β-carboline
Leaves assayed negative with Dragendorff and Ehrlich Reagents.
Wood assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
[Plowman, Schultes & Tovar #7263; Origin: Pebas, Peru (Alpha-Helix 1977)]
Paste:
5-MeO-N,N-dimethyltryptamine
6-MeO-1,2,3,4-tetrahydro-β-carboline
Phloem:
5-MeO-N,N-dimethyltryptamine
Wood assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
[Plowman, Schultes & Tovar #7092; Origin: Pebas, Peru (Alpha-Helix 1977)]
3.2 mg. of alkaloid per 100 grams of Bark:
81% N-methyltryptamine
14% N,N-dimethyltryptamine
4% tryptamine
Trace 5-MeO-N,N-dimethyltryptamine
Trace 5-MeO-N-methyltryptamine
Trace 2-methyl-1,2,3,4-tetrahydro-β-carboline
- Holmstedt et al. 1980
[Prance 15310; Origin: Tapurucuara, Rio Negro, Brazil]
19 mg. of alkaloid per 100 grams of Leaves:
100% DMT
- Holmstedt et al. 1980
Virola loretensis
[Plowman, Schultes & Tovar #7144; Origin: Pebas,Peru (Alpha-Helix 1977)]
Bark assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
[Plowman, Schultes & Tovar #7259[check #!!]; Origin: Pebas,Peru (Alpha-Helix 1977)]
Bark assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
Virola melinonii
[Prance #11035; Origin: Rio Mucajai] Leaves assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
[Schultes & Rodrigues #26153a; Origin: Manáos, Brazil]
0.18 mg. of DMT in 100 gm. of bark
- Holmstedt et al. 1980
Virola multinerva Ducke
[Schultes #24614; Origin: Manáos,Brazil]
1 mg. of alkaloid / 100 gm. of dry bark:
N,N-dimethyltryptamine
1 mg. of alkaloid / 100 gm. of dry roots:
59% 5-methoxy-N,N-dimethyltryptamine
41% N,N-dimethyltryptamine
Dry leaves: Negative results with Dragendorff and Ehrlich Reagents.
- Agurell et al. 1969
[Schultes # 24616; Origin: Manáos, Brazil]
1 mg. of alkaloid / 100 gm. of dry bark:
N,N-dimethyltryptamine
- of alkaloid / 100 gm. of dry flowering shoots.
- of alkaloid / 100 gm. of dry leaves.
- Agurell et al. 1969
Virola pavonis (DC.) Smith
DMT in leaf
- Ott 1994 cited McKenna et al. 1984b
Virola peruviana (DC.) Warburg
DMT and 5-MeO-DMT in bark
- Ott 1994 cited Holmstedt et al. 1980
Virola rufula (A. DC.) Warb.
[Schultes #24612; Origin: Manaus, Brazil]
200 mg. of alkaloid / 100 gm. of dry bark:
95% N,N-dimethyltryptamine
4% 5-methoxy-N,N-dimethyltryptamine
144 mg. of alkaloid / 100 gm. of dry roots:
94% 5-methoxy-N,N-dimethyltryptamine
4% 5-methoxy-N-methyltryptamine
1% N,N-dimethyltryptamine
98 mg. of alkaloid / 100 gm. of dry leaves:
94% N,N-dimethyltryptamine
6% N-methyltryptamine
- Agurell et al. 1969
Virola sebifera Aublet
known by common names of Cuajo Negro and Camaticaro.
Grows in southern part of Venezuela
23 kg. dried milled bark yielded 33 gm (0.14%) sticky basic fraction.
Basic fraction showed one base (DMT) to be present.
β-sitosterol found in neutral fraction ( yield: 0.004%)
Base was purified by dissolving in benzene, chromatographing on 660 grams of alumina and eluting with chloroform; after which the base was distilled at a bath temperature of 80-135° and 0.03 mm.. Yield was as a yellowish oil. Weight of purified product not given.
- Corothie and Nakano 1969
[4.3 kg. of bark analyzed. Neither yields nor place of origin cited. (Venezuela implied)
Sample was provided by Dr. Muça Pires, Museo Goeldi, Belém, Para, Brazil.]
(In order of elution):
N-methyl-N-formyl-tryptamine (non-crystalline)
N-methyl-N-acetyl-tryptamine (non-crystalline)
2-methyl-1,2,3,4-tetrahydro-β-carboline
N,N-dimethyltryptamine
N,N-dimethyltryptamine-N-oxide
N-methyltryptamine
- Kawanishi et al. (1985)
[Prance #12308; Origin: Serra da Moa, Acre, Brazil]
Leaves assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
Virola surinamensis
[Plowman, Schultes & Tovar #6198; Origin: Pebas, Peru (Alpha-Helix 1977)]
Bark assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
[Plowman, Schultes & Tovar #6619; Origin: Pebas, Peru (Alpha-Helix 1977)]
Bark assayed negative with Dragendorff and Ehrlich Reagents.
Leaves assayed negative with Dragendorff and Ehrlich Reagents.
Seeds assayed negative with Dragendorff and Ehrlich Reagents.
Aril assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
[Plowman, Schultes & Tovar #6684; Origin: Pebas, Peru (Alpha-Helix 1977)]
Bark assayed negative with Dragendorff and Ehrlich Reagents.
Leaves assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
[Plowman, Schultes & Tovar #6775; Origin: Pebas, Peru (Alpha-Helix 1977)]
Bark assayed negative with Dragendorff and Ehrlich Reagents.
Paste assayed negative with Dragendorff and Ehrlich Reagents.
- Holmstedt et al. 1980
Virola theiodora (Benth) Warburg
128 gm of leaves and stems gave 93 mg. of crude basic fraction. They were unable to find substituted tryptamine (negative vanUrk's) and did not investigate further.
235 gm. of bark yielded 40 mg. of crude basic fraction;
from 10 mg. of which the following was isolated:
1 mg. of 2-methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline
1 mg. of N,N-dimethyltryptamine
2 mg. of N-methyltryptamine
and 2 components which were not identified
- Cassady et al. (1972) in Mothes; pp.95-99
[Schultes #24595; Origin: Manaos, Brazil]
250 mg. of alkaloid / 100 gm. of dry bark:
52% N,N-dimethyltryptamine
43% 5-methoxy-N,N-dimethyltryptamine
4% 6-methoxy-2-methyl-1,2,3,4-tetrahydro-β-carboline
1% N-methyltryptamine
17 mg. of alkaloid / 100 gm. of dry roots:
63% 5-methoxy-N,N-dimethyltryptamine
22% N,N-dimethyltryptamine
15% 5-methoxy-N-methyltryptamine
470 mg. of alkaloid / 100 gm. of dry flowers: & shoots:
93% N,N-dimethyltryptamine
7% N-methyltryptamine
44 mg. of alkaloid / 100 gm. of dry leaves:
99% N,N-dimethyltryptamine
Tr. 5-methoxy-N,N-dimethyltryptamine
(Holmstedt et al. 1980 says 100% DMT)
- Agurell et al. 1969
[Schultes #24626; Origin: Tototobi, Brazil]
65 mg. of alkaloid / 100 gm. of dry bark:
95% 5-methoxy-N,N-dimethyltryptamine
5% N,N-dimethyltryptamine
21 mg. of alkaloid / 100 gm. of dry leaves:
98% N,N-dimethyltryptamine
2% 2-methyl-1,2,3,4-tetrahydro-β-carboline
- Agurell et al. 1969
Virola venosa (Benth.) Warb.
[Schultes #24613; Origin: Manaus, Brazil] Dry bark: negative results with Dragendorff and Ehrlich Reagents.
1 mg. of alkaloid / 100 gm. of dry roots:
5-methoxy-N,N-dimethyltryptamine
1 mg. of alkaloid / 100 gm. of dry leaves:
N,N-dimethyltryptamine
5-methoxy-N,N-Dimethyltryptamine
- Agurell et al. 1969
Virola based snuff: "Epéna"
[Schultes #24574; Origin: Rio Cauaburí, Brazil] 715 mg. of alkaloid / 100 gm. of snuff:
72% 5-methoxy-N,N-dimethyltryptamine
20% N,N-dimethyltryptamine
4% 2-methyl-1,2,3,4-tetrahydro-β-carboline
2% 6-methoxy-2-methyl-1,2,3,4-tetrahydro-β-carboline
2% N-methyltryptamine
Prepared from Virola theiodora with added dried and powdered Justicia pectoralis var.stenophylla and ashes from Elizabetha princeps
- Agurell et al. 1969
Virola based snuff: "Nyakwána"
[Schultes #24626; Origin: Tototobí, Brazil] ;1,000 mg. of alkaloid / 100 gm. of snuff:
88% 5-methoxy-N,N-dimethyltryptamine
11% N,N-dimethyltryptamine
Tr. N-methyltryptamine
Tr. 5-methoxy-N-methyltryptamine
Tr. 6-methoxy-2-methyl-1,2,3,4-tetrahydro-β-carboline
Prepared from Virola theiodora with no other ingredient
- Agurell et al. 1969