Author Topic: Black Cohosh Contains Tryptamines; Possibly a β-carboline  (Read 2924 times)

0 Members and 1 Guest are viewing this topic.

Offline ―λlτεrηιτγ-

  • Administrator
  • ↼Ȿ♄ꜻϻꜻηĭc⇀ ↽∆ƪc♄εϻĭst⇁
  • *****
  • Posts: 567
  • Karma: +4/-0
  • Gender: Male
  • Herbalism & Kambo
    • View Profile
    • Kambo.me
Black Cohosh Contains Tryptamines; Possibly a β-carboline
« on: April 29, 2016, 08:48:57 pm »
Black cohosh contains

Nω-methylserotonin
5-hydroxytryptamine

and other tryptamine analogues

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3684073/

"Possible occurrence of a β-carboline pathway in the oxidative catabolism of 5-hydroxytryptamine: chemical approach and structure determination of a yellow substance and related β-carboline derivatives. "
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3341503/

and a pubmed article I can't access.
https://www.ncbi.nlm.nih.gov/pubmed/5870459



Ignore information about estrogen effects. It's of no detriment.

It's selective estrogen receptor modulator (SERM) compounds were found to be non-estrogenic and anti-estrogenic at receptors in the hypothalmus, bone, liver, brain, and arteries primarily.

Synthetic SERMS are usually taken with prohormones and steroids by bodybuilders to minimize effects from excess testosterone being converted to estrogens.

Usually SERMs are estrogenic at some receptors and anti at others and the point is to get the benefits of estrogen and none of the negative effects by blocking the receptors from the free-flowing estrogens in the body. The fact that they bind at estrogen receptor sites still makes them estrogens (they still have estrogenic effects).

Natural black cohosh doesn't. It can be used all the time and to greater effect.

Black cohosh binds at these estrogen receptor sites but doesn't cause any estrogen-like effects and is anti-estrogenic, which would mean it would clean any natural estrogens in your body from effecting you by blocking the receptors. Like those artificial estrogens/hormone disrupters like those that are leached from plastic water bottles.



Quote
N-Methylserotonin is found in plants, animals, and fungi. These include the plants, Actaea racemosa (black cohosh)[1] and Zanthoxylum piperitum,[2] the Green and Golden Bell Frog, Litoria aurea,[3] and Amanita mushrooms.[4] The compound binds to several serotonin receptors, including the 5-HT7 and 5-HT1A receptors, with high affinity (IC50 ≤ 2 nM) and selectivity, and displays agonist activity; besides its direct interaction with the serotonin receptors, N-methylserotonin also acts as a selective serotonin reuptake inhibitor.[1]

Quote
United States
N-Methylserotonin is not scheduled at the federal level in the United States,[5] but could be considered an analog (of Bufotenin), in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analog Act.

Florida
N-Methylserotonin is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[6]


Another name for N-Methylserotonin is Norbufotenine! Bufotenin (5-HO-DMT, N,N-dimethylserotonin) is a psychedelic.
"There is a difference between
not remembering
and not dwelling upon.
I choose not to dwell upon the bad,
to me
it's kinda like being in a paradise
but staring at a nearby garbage dump instead.
You define your life by
where you direct your gaze."

Offline ―λlτεrηιτγ-

  • Administrator
  • ↼Ȿ♄ꜻϻꜻηĭc⇀ ↽∆ƪc♄εϻĭst⇁
  • *****
  • Posts: 567
  • Karma: +4/-0
  • Gender: Male
  • Herbalism & Kambo
    • View Profile
    • Kambo.me
Re: Black Cohosh Contains Tryptamines; Possibly a β-carboline
« Reply #1 on: April 29, 2016, 08:54:07 pm »
Quote
Constituents: Constituents of black cohosh with proposed or demonstrated pharmacological activity include triterpine glycosides (23-epi-26-deoxyactein, actein, 27-deoxyactein, cimicifugoside A, cimicifugoside M, cimiracemoside A-H)21,45,46,47,48,12,49,50,51, cyclolanostanol xylosides 52, isoflavonone formononetin 53, hydroxytyrosol 54, actaeaeposcide 55, phenylpropanoids (cimiracemate A, cimiracemate B)8,56, organic acids (caffeic acid, cimicifugic acid A, cimicifugic acid B, cimicifugic acid E, cimicifugic acid F, cinnamic acid ester dehydrocimicifugic A, dehydrocimicifugic acid B, dihydroxyphenyl lactic acid, ferulic acid, fukinolic acid, isoferulic acid, methyl caffeate acid, salicylic acid)8,57,54,58, phenols57, quinoid metabolites of caffeic acid, cimiracemate B, fukinolic acid, fukiic acid, and.hydroxytyrosol54. Actaea racemosa specifically contains lignans (e.g., actaealactone), phenylpropanoid ester derivatives (e.g., cimicifugic acid), polyphenols (0.36-2.92% (w/w) in dried root and rhizome), protocatechuic acid, protocatechualdehyde, p-coumaric acid, caffeic acid, methyl caffeate, ferulic acid, ferulate-1-methyl ester, isoferulic acid, 1-isoferuloyl-beta-d-glucopyranoside, fukinolic acid, and cimicifugic acids A, B, and D-F

Quote
Neuropharmacologic effects: Black cohosh has been shown to exhibit an action on the central endogenous opioid system in postmenopausal women as evidenced by suppression of mean luteinizing hormone pulse frequency following opioid receptor blockade.

http://www.sigmaaldrich.com/life-science/nutrition-research/learning-center/plant-profiler/cimicifuga-racemosa.html


Quote
Black cohosh extract showed inhibitory potential for histamine release

It's an anti-histamine (anti-allergenic) but could possibly cause flushing and itching symptoms at higher doses.

Dextromethorphan (DXM) is like that. Is an anti-histamine but causes histamine release at higher doses.

Erowid lists Black Cohosh as a "Mild Sedative; Anti-spasmodic". No reports.



Also reading seeing shit on webmd like:

"Breast cancer: There is some concern that black cohosh might worsen existing breast cancer. Women who have breast cancer or who have had breast cancer in the past, and women at high-risk for breast cancer, should avoid black cohosh."

I'm reading multiple studies about it helps breast cancer in
Herbal Contraindications and Drug Interactions plus Herbal Adjuncts With Medicines
The agenda of the pharmaceutical industry and it's medical community of pushers is strong.



Quote
Black Cohosh behaves as a mixed competitive ligand and partial agonist at the human mu opiate receptor
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2547488/



Quote
The first medicinal use of black cohosh is generally attributed to Native Americans, who used black cohosh for the treatment of a variety of disorders, including various conditions unique to women such as amenorrhea and menopause, rheumatism, kidney disorders, malaise, and pain during menses and childbirth
Quote
Dr. John King claimed that Macrotys was a remedy of “abnormal conditions of the principal organs of reproduction in the female”, and the roots “very efficacious in the treatment of chronic ovaritis, endometriosis, and menstrual derangements, such as amenorrhea, dysmenorrhea”
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2547488/

Dopamine receptor activity:
Quote
Dopaminergic activity in the CR extract BNO 1055 could be demonstrated with the D(2)-receptor assay. A countercurrent chromatography resulted in a separation of estrogenic and dopaminergic activity in two distinct fractions.
https://www.ncbi.nlm.nih.gov/pubmed/12609557/

So activity at serotonin, dopamine, and opioid receptors.



5-MeO-DMT, Bufotenin, DMT, LSD, MDA, MDMA, Mescaline, Psilocin are all also 5-HT1 A agonists.

http://www.biopsychiatry.com/psilocybin.htm
http://pharmacologycorner.com/serotonin-5ht-receptors-agonists-antagonist/

Black Cohosh also has affinity at 5-HT1D which LSD also agonizes.
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3684073/

Buspirone (antidepressant) is a 5-HT 7 agonist and is known to cause hallucinations.

http://www.ehealthme.com/ds/buspar/hallucinations
https://treato.com/Buspar,Hallucinations/?a=s
"There is a difference between
not remembering
and not dwelling upon.
I choose not to dwell upon the bad,
to me
it's kinda like being in a paradise
but staring at a nearby garbage dump instead.
You define your life by
where you direct your gaze."

Offline ―λlτεrηιτγ-

  • Administrator
  • ↼Ȿ♄ꜻϻꜻηĭc⇀ ↽∆ƪc♄εϻĭst⇁
  • *****
  • Posts: 567
  • Karma: +4/-0
  • Gender: Male
  • Herbalism & Kambo
    • View Profile
    • Kambo.me
Re: Black Cohosh Contains Tryptamines; Possibly a β-carboline
« Reply #2 on: April 29, 2016, 09:12:27 pm »
Norbufotenin Structure
https://en.wikipedia.org/wiki/N-Methylserotonin#/media/File:Norbufotenine.svg

Vs.

Bufotenin Structure
https://upload.wikimedia.org/wikipedia/commons/0/04/Bufotenin_structure.svg


Also started a thread inquiring for more information at https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=70650



Quote
N-Methylserotonin. 5-Hydroxy-N-methyltryptamine.
http://www.chemspider.com/Chemical-Structure.132989.html

So this would be 5-HO-NMT.

http://isomerdesign.com/PiHKAL/explore.php?domain=tk&id=5131

So as with NMT and Bufotenin it is probably destroyed by mono amine oxidase.

Quote
NMT has been found in the bark, shoots and leaves of several plant species, including Virola, Acacia, Mimosa and Desmanthus
Quote
Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.[3] However, it may become active upon combination with a MAOA inhibitor (MAOI).[3] By vaporization NMT shows activity at 50–100 mg, with a duration of 45–70 minutes; duration of visual effects 15–30 seconds. Effects are primarily non-visual.
https://en.wikipedia.org/wiki/N-Methyltryptamine

^^And most of us thought the effects of those plants were just DMT and possibly 5-MeO-DMT!

So as I posted there's probably a Beta-carboline in Black Cohosh, but this seems to me to open a doorway of possible Harmine plus 5-Ho-NMT or NMT containing plant decoctions for new natural ayahuasca-type analogues.

Or at least Harmine + Black Cohosh root extraction might probably enhance the effects.
Now looking into plants with high quantities of clean sources of 5-HO-NMT or NMT.

TiHKAL Norbufotenin entry: http://isomerdesign.com/PiHKAL/explore.php?domain=tk&id=5131



Not great at deciphering this page but

Quote
Compound 53 had an elemental composition containing two hydrogens less than 58 and 59 (C12H12N2O), suggesting a dihydro-β-carboline structure. The ready loss of a methyl radical (m/z 186), along with the fragment ion of m/z 170, [MH-CH3NH2]+, indicated that the N(2) nitrogen on the β-carboline ring was methylated. Biosynthetic considerations were used to deduce the position of the double bond on the β-carboline ring. Accordingly, the most likely position of the double bond is 1,2 which was confirmed by comparison of retention time and fragmentation pattern with authentic N(2)-methyl-6-hydroxy-3,4-dihydro-β-carboline. Biosynthetically, this compound is likely formed by dehydrogenation of 58 and represents a new natural product. It should be noted that dihydro-β-carbolines are often by-products of Pictet-Spengler condensation [58]. Thus, it is possible that 58 is an isolation artifact.

Quote
The product ion spectrum of compound 46 eluting at 10.6 min during LC-MS of fraction 4 was dominated by an ion of m/z 144 with the elemental composition (C10H13N2), corresponding to protonated tryptamine. In-source fragmentation followed by MS-MS product ion analysis of m/z 144 showed a fragmentation pattern identical to authentic tryptamine, suggesting that this compound is a tryptamine derivative. The neutral loss of iminoacetic acid (C2H3NO2) combined with database searching suggested that 46 might be a tetrahydro-β-carboline carboxylic acid. Since two positional isomers (1 and 3-substituted) are known, both analogs were synthesized and compared with 46. These experiments identified 46 as 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid,
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3341503/

Sounds like at least 2 beta-carbolines, possibly
N(2)-methyl-6-hydroxy-3,4-dihydro-β-carboline
1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

Or similar structures. So the fact that it has beta-carbolines and is used as a classic herbal medicine with really no information or reports on toxicity or overdosing suggests at least some evidence that the compounds in this plant are possibly safe with MAO inhibited?

Also based on that a list of quinoline alkaloids with potential psychoactive effects to research.

salsolinol
norsalsolinol (6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline)
norcoclaurine
reticuline, 6,7-dihydroxy-1-methyl-3,4-dihydroisoquinoline
1,2-dehydrosalsolinol
Aporphine 5-HT1 A and D2 agonist (found in blue lotus)

Quote
Aporphine and its related alkaloids bulbocapnine, boldine, glaucine and corytuberine are antipsychotic, exert naloxone-reversible antinociceptive (reducing sensitivity to painful stimuli) activity and with the exception of corytuberine are anticonvulsant.
https://en.wikipedia.org/wiki/Aporphine

How has no one reported psychoactive effects of this plant beyond a sedative?
This plant has my head spinnin'.

norcoclaurine:
Quote
In a rodent model, it was found that higenamine (norcoclaurine) produced cardiotonic, vascular relaxation, and bronchodilator effects.[8][9] In particular, higenamine, via a beta-adrenoceptor mechanism, induced relaxation in rat corpus cavernosum, leading to improved vasodilation and erectile function.

Related to improved vasodilatory signals, higenamine has been shown in animal models to possess antiplatelet and antithrombotic activity via a cAMP-dependent pathway, suggesting higenamine may contribute to enhanced vasodilation and arterial integrity.[2][7][9][10]
https://en.wikipedia.org/wiki/Higenamine

Quote
Reticuline is one of the alkaloids found in opium, and experiments in rodents suggest it possesses potent central nervous system depressing effects.[3] It is the precursor of morphine and many other alkaloids.
https://en.wikipedia.org/wiki/Reticuline
« Last Edit: April 30, 2016, 03:23:36 am by λlτεrηιτγ »
"There is a difference between
not remembering
and not dwelling upon.
I choose not to dwell upon the bad,
to me
it's kinda like being in a paradise
but staring at a nearby garbage dump instead.
You define your life by
where you direct your gaze."

Offline ―λlτεrηιτγ-

  • Administrator
  • ↼Ȿ♄ꜻϻꜻηĭc⇀ ↽∆ƪc♄εϻĭst⇁
  • *****
  • Posts: 567
  • Karma: +4/-0
  • Gender: Male
  • Herbalism & Kambo
    • View Profile
    • Kambo.me
Re: Black Cohosh Contains Tryptamines; Possibly a β-carboline
« Reply #3 on: April 30, 2016, 03:24:31 am »
Quote
So I popped one pill, and awaited its effects. The effects came on relatively quickly. I felt slightly sedated, so I plopped on my bed for a nap.

I looked at the ceiling and the walls seem to be moving slightly, and it looked like my rods and cones were more visible than usual. Just minor benadryl-like hallucinations.

It reminded me of kava kava herb which is a sedative and mild psychedelic.
https://erowid.org/experiences/exp.php?ID=67354
"There is a difference between
not remembering
and not dwelling upon.
I choose not to dwell upon the bad,
to me
it's kinda like being in a paradise
but staring at a nearby garbage dump instead.
You define your life by
where you direct your gaze."