..from researching the MAOI effects of various flavonoids, i am inspired to start a Passiflora thread.. some contain useable amounts of harmala alkaloids, but much of the sedative/action of these species is due to flavonoids..more on this later.
..northern hemispherians can perhaps bask in warm notions of growing some next spring..in fact some of the biggest collections of grown world-wide passifloras are in Germany and the Netherlands..

the following list is taken mainly from Voogelbreinder (2009), which has an excellent passiflora section, there are around 600 species worldwide found mostly in C. and S. America & the Caribbean, with a few in N. America, Africa, the Pacific & Australia..symbiotic butterflies who graze them also contain similar harmala alkaloids..one species (Passiflora xiikzodz)is known only from mayan temple ruins..

Passifloras containing Harmala alkaloids or known to be sedative/psychoactive:

P. actinia
P. alata (Wing-stemmed Passionflower)
P. alba (White Passion Vine)
P. biflora (Two-flowered Passionflower)
P. byroniodes (‘cocapitos’)
P. caerulea (Blue Passionflower)
P. capsularis (‘calzoncillo’)
P. coccinea (Red Passionflower)
P. costaricensis
P. x decainseana
P. edulis (Common Passionfruit - several varieties)
P. eichleriana
P. foetida (Stinking Passionflower)
P. hibertiana
P. incarnata (Passionflower herbal)
P. involucrata (‘chontay huasca’)
P. jorullensis (‘coanenepilli’)
P. ligularis
P. mollissima (Bannana Passionfruit)
P. murucuja (Dutchman’s Laudanum)
P. oerstedii
P. quadrangularis (Giant Granadilla)
P. quitensis
P. rubra (Dutchman’s Laudanum)
P. suberosa (Cork-barked Passionflower)
P. supbeltata
P. vespertilio (Bat-winged Passionflower)
P. warmingii
(28 in total. so far)

i’ll look at each one in more detail soon..it is known that p. incarnata can be used to orally activate tryptamines (see Harmine In Passiflora Caerulea -)..there are other possibilities awaiting discovery..
..anyone with Passiflora knowledge’ s input is much appreciated (be it growing them, wild sightings, medicinal use, or chemistry reports)
.

below is the herbal medicinal ‘passionflower’ Passiflora incarnata, native southern USA (though the flowers are not actually the part used for anti-depressant/sedative effects, except perhaps visually);
and below that is Passiflora xiikzodz, a presumed Mayan cultivar...

..let's start with the rarest, which has fortunately been in cultivation since the early '90s thanks to it's researcher
Rob Montgomery (of Of The Jungle)

Passiflora involucrata is used as an entheogen and ayahuasca additive by the Yahua of Peru..it was sometimes added to a b.caapi brew instead of (though often with) p.viridis or diploteris spp..
..when asked why it was added, a shaman responded "to make the visions even more colorful.." (i.e. even more than with the tryptamine plant alone) [ref. Of The Jungle newsletter 1993] ..i know of no chemical studies..

the Yahua call it 'chontay huasca'...

..also in Peru (according to Voogelbreinder 2009) the liquified fruit of Passiflora quadrangularis is taken as a sedative..in Brazil the rinds are used for the same purpose, the roots are said to be abortifacient and narcotic (perhaps depending on dosage), stems claimed 'toxic' (see below)

..it is very widely grown for it's fruit, and as an ornamental, also known as 'Giant Granadilla'
the roots contained unquantified levels of Harman [Neu 1954]; the leaf small amounts of
serotonin, norepinephrine & tryptamine [Applewhite 1973; Smith 1977];
cyanogenic glycosides were found in the stem & foilage..i will discuss these more later..they can be toxic but are destroyed by prolonged drying, heating, or pyrolysis..most unknown passifloras should probably be subjected to some heat or drying before bioassay to be sure there are no glycosides..

i have heard one underground reprort of use of P. quadrangularis root and rind extract as a 'relaxant'..

..future posts will describe a few successful (and enjoyable) findings of anti-depressent or MAOI effects and psychoactivity from other passifloras, and the action of flavonoids, believed to be the most active components of herbal passionflower and blue passionflower..
.

..& this is a nice one..Passiflora murucuja, known in the West Indies as 'Dutchman's Laudanum', where "it is considered an excellent substitute for opium." [Voogelbreinder 2009]..water and alcohol extracts have been used as a "safe and effective narcotic" [Cook 1860]
.

..so once again Passiflora incarnata

this is the first time the details of a 1994 p. inacarnata + acacia extract huasca experiment have been released outside of the ethnobotanic research community: (an incarnata vaporized extract experiment is referred to in Voogelbreinder 2009)

"...approx. 1kg of purchased dry passiflora incarnata stem & leaf was boiled X3 in rain water...the large amount of liquid was combined and reduced over several hours, turning increasingly dark purple/brown and thick..,while still possible it was filtered several times through fine cheesecloth...a point of viscosity was reached at which 1 hypothesized dose (333grams of herb) equalled a large glass or coffee mug of thick liquid (the aromas during the process were noted to be somewhat mildly psychoactive)
...A dosage of estimated at = 400 grams herb was consumed by two subjects...5 minutes afterwards approx. 50-70mg of a. obtusifolia extract as the freebase was rapidly swallowed and chased with water/lemon juice (to remove the awful freebase aftertaste)
...Within 10 minutes strong sedative and 'anti-depressant' effects from the passiflora were felt...as these grew (without yet tryptamine effects) it was commented that this plant alone was a satisfying experience...A shiny and pleasant 'haze' surrounded lights...At around 90 minutes, after it was pondered that maybe MAO inhibition was not sufficient, tryptamine-like effects (geometries, '4D-ness', auditory) rapidly grew over 10 minutes accompanied by sudden purging...
...Both subjects found the intensity of colors beyond their previous experiments with a. extract and p. harmala or b. caapi...'fantastic bright blues, reds, purples and golden hues.'...It was subjectively judged as more sedative or narcotic than rue or caapi with a strong 'dreaminess'...rue was judged the 'clearest', caapi unique in other ways...
'It made the tryptamines very dreamy, colorful, and beautiful...very feminine.'
...After a linear 'plateau' of 30 minutes, effects gradually subsided over 2-4 hours, with a sense of sedation up to 5hrs afterwards. Overall, it was very positive...'It lacked the punch of rue, but had such a lovely dreamy quality...very sensual...'..."

it is possible some of the MAOI activity was due to the flavonoids Apigenin and Kaempferol, as well as the ß-carbolines harmine, harmaline, harman, norharman and harmol (present at 0.1-0.2% [Hultin]; Gracie & Zarkov claim up to 0.5%)
Flavinoids are present at around 1.5%,or more, in stems and leaves..regarding Kaempferol, also found in Ginkgo biloba, from:
B. D. Sloley et al.
["Identification of Kaempferol as a Monoamine Oxidase Inhibitor and Potential Neuroprotectant in Extracts of Ginkgo Biloba Leaves" Journal of Pharmacy and Pharmacology Volume 52, Issue 4, pages 451–459, April 2000]


some potent MAOI flavonoids include quercitrin, isoquercitrin, rutin, and quercetin, which were isolated from the leaves of Melastoma candidum. They exhibited an inhibitory effect on MAO-B. The IC50 values 19.06, 11.64, 3.89, and 10.89 μM respectively/
["Monoamine Oxidase B and Free Radical Scavenging Activities of Natural Flavonoids in Melastoma candidum "
Mei-Hsien Lee et al. J. Agric. Food Chem., 2001, 49 (11), pp 5551–5555]

..many more plants than previously thought could be effective MAO inhibitors..

i have attached a cool paper on flavonoids and their bio-activity
"Flavonoids and the CNS" Anna K. Jäger and Lasse Saaby Molecules 2011, 16, 1471-1485
.

..Voogelbreinder (2009) mentions a successful MAOI activation of dmt freebase (& i can also confirm/add acacia leaf) utiliszing the widely grown
Passiflora coccinea (red 'grandilla' leaf & stem..
..an experiment i witnessed in 2002 leaf and stem of coccinea (150-200grams per person) were boiled 3 times in water with a dash of white vinegar and acacia longifolia var. leaf (approx 40 grams)
..this led to strong MAOI effects, the onset of visuals within an hour..it was difficult to remain 'alert' during the strongest effects..the action was not as 'warm' or 'anti-depressant' as p. incarnata..it was found that MAOI effects lingered long after tryptamine visuals had finished..8 hours in one person, and up to 12 in another..this included 'haziness' of vision, light sensitivity, sedation (not unpleasant) and diet sensitivity..the different action to p. incarnata may be due to differing Flavonoids, which have also not been tested in the plant..the experiment was conducted based on some south american ethnobotanical data (used as a decoction in the Amazon to treat fever [Duke & Vasquez 1994]))

P. coccinea has not been tested for alkaloids, but was found to contain passicocccin, a cyanogenic glycoside..such glycosides can be quite toxic, but are destroyed by drying or prolonged heating..

the dried leaf can be smoked for very pleasant effects.. the fruit (and flowers) are edible..

..ingestion or smoking of p. incarnata extracts can lead to extraordinary potentiation and duration extension of smoked tryptamines (as also found by a few sources now) ..concentrated enough base extracts are visual/entheogenic on their own (as also reported in Voogelbreinder 2009) ..a recent thread had a subthreshold oral tryptamine but groovy sounding fresh incarnata experiment..

another very likely MAOI candidate (and who knows, could be stronger) is Passiflora caerulea (Blue Passionflower)
it is similar to P. incarnata in harmala alkaloid content, and differs in flavonoids in containing Chrysin (also an MAOI)
Chrysin is sold as a mood enhancer in the health supplements scene..cearulea also contains kaempferol, found in incarnata..
like incarnata it's ingestion is known to be fairly safe..
.

...was wondering if any know goodies are in passiflora laurifolia? also what kind of effects can be found from smoking dried p. incarnata leaf? read somewhere that maoi effects are stronger when smoked?....

..i have no idea about p. laurifolia, but all passifloras are potentially interesting..
re: smoking of dried leaf p. incarnata leaf - S. Voogelbreinder reports from a few sources (including personal obsv. ) that it produces 'cannabis-like effects'.
i would describe it as anxiolytic/relaxant and good also for nicotine withdrawl..
..effects of some MAOI compounds can be stronger (& shorter duration) when smoked, however except for p. harmala, concentrated extracts would be required..
.

Awesome thread nen, thanks for sharing the details! I will be coming back to this thread sometime in the future, this needs more research

..thank you endlessness , look forward to hearing of your and others views and research on these matters,
in the mean while..
..regarding Flavonoids generally,
from the abstract of the excellent Flavonoids and the CNS (Jåger ans Saaby 2011)


The lists below are not complete, but a sample

Plant Flavonoids with inhibition of MAO-A, MAO-B, or both: (refs: see below)
apigenin (P. incarnata, Matricaria retutica (camomile), Tanacetum parthenium (feverfew), Sersia dentata (Anacardiaceae) )
catechin & epicatechin (Uncaria rhynchophylla (Rubiaceae) )
cyanidin
chrysin (P. caerulea)
delphinidin
formononetin (Sophora flavescens)
genistein
kaempferol (Gingko biloba, P. caerulea, P. incarnata, Tilia americana var. mexicana (linden flowers)
kushenol F (Sophora flavescens)
quercetin (Calluna vulgaris (Heather - Ericaceae), G. biloba, Melastoma candidum, Tilia americana, various plants)
quercetrine (Melastoma candidum)
isoquercetin (Melastoma candidum)
malvadin
naringenin (Mentha aquatica, Citrus (oranges) )
pelargonidin (Fragaria × ananassa - strawberries)
peonidin
petunidum
rutin (Acacia polyacantha spp. camplyacantha, Melastoma candidum)
vitexin (several Passifloras, Acacia senegal leaves)

Plant flavones and flavonoids with GABA-A-benzodiazepine affinity:
apigenin (also MAOI) (Matricaria retutica, P. incarnata, Tanacetum parthenium,S. dentata (Anacardiaceae) )
6-methylapigenin
agathisflavone (Sersia pyroides (Anacardiaceae) )
cirsilincol (Artemisia herba-alba (Asteraceae) )
chrysin (also MAOI) (Passiflora caerulea)
dinatin (Artemisia herba-alba)
hispidulin (Artemisia herba-alba)
ororylin (Scuttelaria baicalensis)
skrolfulein (Artemisia herba-alba)

..this list is by no means complete..also, bear in mind this is a relatively new field of research, and many more plants have not been tested for flavonoids (or alkaloids, for that matter) if anyone knows other plant sources of any of these i'd love know..

References: (the Jåger and Saaby 2011 paper attached earlier, plus)

1. Viola, H.; Wasowski, C.; Destein, M.L.; Wolfman, C.; Silveira, R.; Dajas, F.; Medina, J.H.; Paladini, A.C.
Apigenin, a component of matricaria recutita flowers, is a central benzodiazepine receptors ligand with anxiolytic effects.
Planta Med. 1995, 61, 213-216.
2. Aguirre-Hernandez, E.; Gonzalez-Trujano, M.E.; Martinez, A.L.; Moreno, J.; Kite, G.; Terrazas, T.; Soto-Hernandez, M.
HPLC/MS analysis and anxiolytic-like effect of quercetin and kaempferol flavonoids from Tilia americana var. mexicana.
J. Ethnopharmacol. 2010, 127, 91-97.
3. Mullen, W.; Archeveque, M.A.; Edwards, C.A.; Matsumoto, H.; Crozier, A. Bioavailability and metabolism of orange Juice flavanones in humans:impact of a full-fat yogurt. J. Agr. Food. Chem. 2008, 56, 11157-11164.
4. Kavvadias, D.; Sand, P.; Youdim, K.A.; Qaiser, M.Z.; Rice-Evans, C.; Baur, R.; Sigel, E.; Rausch, W.D.; Riederer, P.; Schreier, P.
The flavone hispidulin, a benzodiazepine receptor ligand
with positive allosteric properties, traverses the blood-brain barrier and exhibits anticonvulsive effects.
Br. J. Pharmacol. 2004, 142, 811-820.
5. Avallone, R.; Zanoli, P.; Puia, G.; Kleinschnitz, M.; Schreier, P.; Baraldi, M. Pharmacological profile of apigenin, a flavonoid isolated from Matricaria chamomilla.Biochem. Pharmacol. 2000,
6. Wolfman, C.; Viola, H.; Paladini, A.; Dajas, F.; Medina, J.H. Possible anxiolytic effects of chrysin, a central benzodiazepine receptor ligand isolated from Passiflora caerulea.
Pharmacol. Biochem. Behav. 1994, 47, 1-4.
7. Pedersen, M.E.; Vestergaard, H.T.; Stafford, G.I.; van Staden, J.; Jager, A.K. The effect of extracts of Searsia species on epileptiform activity in slices of the
mouse cerebral cortex.
J. Ethnopharmacol. 2008, 119, 538-541.
8. Fernandez, S.P.; Wasowski, C.; Paladini, A.C.; Marder, M. Synergistic interaction between hesperidin, a natural flavonoid, and diazepam.
Eur. J. Pharmacol. 2005, 512, 189-198.
9. Sloley, B.D.; Urichuk, L.J.; Morley, P.; Durkin, J.; Shan, J.J.; Pang, P.K.T.; Coutts, R.T.
Identification of kaempferol as a monoamine oxidase inhibitor and potential neuroprotectant in extracts of Ginkgo biloba leaves.
J. Pharm. Pharmacol. 2000, 52, 451-459.
10. 59. Lee, M.H.; Lin, R.D.; Shen, L.Y.; Yang, L.L.; Yen, K.Y.; Hou, W.C. Monoamine oxidase B and
free radical scavenging activities of natural flavonoids in Melastoma candidum D. Don. J. Agr.
Food. Chem. 2001, 49, 5551-5555.
11. Chimenti, F.; Cottiglia, F.; Bonsignore, L.; Casu, L.; Casu, M.; Floris, C.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.;
Ortuso, F.; Trombetta, G.; Loizzo, A.; Guarino, I.
Quercetin as the active principle of Hypericum hircinum exerts a selective
inhibitory activity against MAO-A: Extraction, biological analysis, and computational study. J. Nat. Prod. 2006, 69, 945-949.
12. Hwang, J.S.; Lee, S.A.; Hong, S.S.; Lee, K.S.; Lee, M.K.; Hwang, B.Y.; Ro, J.S.
Monoamine oxidase inhibitory components from the roots of Sophora flavescens. Arch. Pharmacal. Res. 2005, 28, 190-194.
13. Olsen, H.T.; Stafford, G.I.; van Staden, J.; Christensen, S.B.; Jager, A.K. Isolation of the MAO-inhibitor naringenin from Mentha aquatica L.
J. Ethnopharmacol. 2008, 117, 500-502.
14. Van Praag, H.; Lucero, M.J.; Yeo, G.W.; Stecker, K.; Heivand, N.; Zhao, C.; Yip, E.; Afanador, M.; Schroeter, H.; Hammerstone, J.; Gage, F.H.
Plant-derived flavanol (-)epicatechin enhances angiogenesis
and retention of spatial memory in mice. J. Neurosci. 2007, 27, 5869-5878.
15. Vafeiadou, K.; Vauzour, D.; Lee, H.Y.; Rodriguez-Mateos, A.; Williams, R.J.; Spencer, J.P.E.
The citrus flavanone naringenin inhibits inflammatory signalling in glial cells and protects against neuroinflammatory injury.
Arch. Biochem. Biophys. 2009, 484, 100-109.

..will look at a few other passifloras containing harman and harmol soon...

..Passiflora foetidia (Stinking Passionflower) leaves were used in India to treat headache and dizziness [Nadkarmi 1976]. It has yeilded small amounts of Harman and Serotonin, glycosides, and the flavonoid anthocyanin malvidin-3-monoside [see Voogelbreinder 2009 for various refs]..in Mexico it is considered an opium substitute, 'amapola'..It has several recognised sub-species and is also known in Jamacia as P. hispida, where it is used as a 'narcotic' [Pammel 1911]

..while in the West Indies, Passiflora rubra is also known as 'Dutchman's Laudanum', and in Equador the fruits are considered narcotic..there are no chemical studies i'm aware of..a decoction of the flowers was reported to Voogelbreinder as a 'pleasant-tasting-potent-sedative'..

below are 2 pics each of P. foetida (synon. P. hispida) and P. rubra:

..and here's a promising one: Passiflora alata is used in Brazil to treat anxiety and insomnia..the leaf contained the ß-carboline Harman (0.082%) and 4.48% Flavonoids which were Vitexin, isovitexin, isoorientin, and 2"-xylosylvitexin [Oga et al. 1994]..the roots contained 0.13% Harman, and 0.15% maracugine [Neu 1954]..according to a wikipedia portuguese translation, Maracujina "..is a sedative drug for the treatment of states of nervous excitement, consisting of active plants, classics in the Brazilian Pharmacopoeia as Passiflora Alata, known neurossedativos."

Harman (and Harmol) were of previously unclear pharmacology as to MAO inhibiton, but a fairly recent paper which found these two ß-carbolines in raisin extracts demonstrated that they had MAOI effects [see
Identification and Occurrence of β-Carboline Alkaloids in Raisins and Inhibition of Monoamine Oxidase (MAO)..harman is also found in in some acacias..
.
P. alata (Brazil)

..acidentally had a mislabeled photo for P. rubra, which i've fixed..it was actually P. caerulea var. "amethyst", a horticultural cultivar, and very pretty so i'll keep it in the thread...

I made a tea from 1 Passiflora quadrangularis flower a couple years back and I had a lot of dark chocolate that day. The effects were psychedelic, but I also felt quite sick. Sparkly visuals and neon wave functions present behind closed eyelids. It reminded me of a very nauseating and broncho-constrictive acid trip. I remember it was so bad I had to ask people on the chat how to counter it, and benzyme told me to eat a bunch of black pepper ;] I found lower doses of Passiflora quadrangularis as a tea without the dark chocolate to be sedative. Unforunately, my vine died last year so I no longer have this specimen. Thanks for the great list nen888 I really can't wait to explore the passionflowers more.

..very interesting, thanks ۩ ..i wonder how the chocolate and probable MAOI compounds in the giant grandilla were interacting? ..so the cocoa was both enhancing the effects and creating nausea? ..i usually avoid chocolate with ayahuasca, but maybe it can be an enhancer if the nausea is combatted..
i'm sensitive to MAOIs (especially rue) and would expect to have a very nauseating slightly toxic time if i ate chocolate (especially with sugar), but everyone's dfferent..
..from what info. i can find the best parts of P. quadrangularis to use would be root or fruit rind...

..hey actually ۩ it just sunk in that you only used 1 flower! ..that's unprecedented..this needs more research,
P. quadrangularis is a very widely grown and easily available vine..
the flowers of P. incarnata don't seem to have effects, but me and some friends found that adding 5-8 P. coccinea leaves to rue based hoasca added a slight extra colourful and relaxing dimension that the rue lacks by itself..

..all these species are grown successfully in glass-houses in northern Europe..some of the biggest collections in the world are in Germany and the Netherlands

the groovy thing about passionfruit vines is that they don't strangle or harm trees that they grown on,
..i quite like growing passion vines with my acacias..
.

..the common edible passionfruit Passiflora edulis has numerous varieties..the fruit juice is known to have mild sedative effects [Lutomski et al. 1975]

..it is used by indigenous tribes of Paraquay in conjunction with the cactus Pereskia scandens ( 'ysypovori' ) as an entheogen [Stuart 2002 in Entheogen Review 11(2); 58-61; Voogelbreinder 2009 p269]..P. scandens has been found to contain small amounts of mescaline and tyramine [Doetsch et al. 1980]
P. edulis is used in Malawi to treat insomnia, migrane and epilepsy, and in Brazil the fruit rind is used as a sedative tea [Duke and Vasquez 1994]
..P. edulis leaf and fruit have yielded small amounts of the ß-carboline Harman..the fruit juice also contained small amounts of harmine, harmol and harmaline, and flavonoids incl. rutin, vitexin and quercetin (see flavonoid MAOIs above)
it is a relative of P. incarnata and caerulea, and while not nearly as strong in effects, nonetheless has some in sufficient amounts..
here's a link to another groovy passionflower thread: Passionflower as MAOI

other Passifloras not mentioned yet which contained Harman include P. actinia [with maracugine], P. alba, P. byronoides, P. capsularis, P. eichleriana (with maracugine), P. suberosa and P. warmingii [Neu 1954]..
..i'm still uncertain as to the structure of maracugine, also found in P. alata..will keep researching..
.

below are P. eichleriana and P. suberosa (corky passionvine)

Great thread !

About Passiflora Caerulea...

In this part of the Balkan region where i live, the Blue Passiflora's are quite common specie.I found out that it is very good candidate for MAO - inhibiting alkaloids ( if this vine grows in abundance somewhere near you ).

Recently i was experimenting on extraction with harvested plant material from a very big vine growing in my neighborhood. The vine is around 4 or 5 m in height and the thickness of the vine is around 5 cm in diameter. It is probably older than 5 years and it grew all around a big pine tree. In summer the three is completely covered with the flowers of the Passiflora, really amazing sight !

Anyway, i did an extraction with 500 g of still green fresh material following Gibran's method for harmala alkaloids except for few tweaks i implemented which were more suiting for my situtation (great pictorial btw) . After the reduction of the liquid containing the salts i used NaOh to basify and there was instant precipitation in the liquid. I have made a small pictorial which i will post in the harmala section.I will add all the details from the extraction there and i will link the thread here if i find how to do that.

..hey that's fantastic Ambivalent..! many have been asking about passiflora harmala extraction in the past few months..