So each time I send a plant extract to analyse, when I get the results, each peak needs to be identified

I have a program which identifies some of the main compounds automatically, and Ive been gaining some experience with the different analysis we are doing to identify some of the others, but there are still many peaks I cannot identify and its taking me a LOT of time to try to find it out.

So here's where I need help from you guys (and gals) to help me with: To go through literature (publications linked in analysis threads in my signature, + google scholar searches) and collect information on the alkaloids listed below. Also making a list of all the alkaloids that were found so far in these particular plants we've been studying

You dont need to be a chemist to do this, just browse through publication in search for the alkaloid information. The information im looking for is: Alkaloid mass weight, mass spectra (which can either come as a graph, or as numbers for example something like M+203(8.9), 158(1OO), 103(13.7) , UV spectra (graph or numbers), any other analytical data, and a drawing of molecular structure is nice too. You dont need to find everything, every small info added here is great!

I will list the plants/alkaloids we need information from (feel free to suggest additions to the list, of alkaloids that are found in the plants or typical impurities that can be found)

So here are the plants and alkaloids we need more info from:

Banisteriopsis caapi
Harmine, harmaline, THH
Banistenoside A
Banistenoside B
Shihunine
Dihydroshihunine
harmic acid methylester
harmalinic acid
harmic amide
acetyl norharmine
ketotetrahydronorharmine
tetrahydronorharmine
β-d-fructofuranosyl-(2 → 5)-fructopyranose

Tabernaemontana sananho (posted here)
Coronaridine
Heyneanine
3-Hydroxycoronaridine
Ibogamine
Voacangine

Phalaris spp.
All alkaloids listed here, except gramine, hordenine, DMT, NMT and 5-MeO-DMT, all of which I already have the info.

Syrian rue
harmine
harmaline
harmane
harmol
harmalol
tetrahydroharmine
vasicine (peganine)
deoxyvasicine (deoxypeganine)
vasicinone
deoxyvasicinone
pegamine
peganidine
isopeganidine
deoxypeganidine
dipegine
dipeginol
ruine
dihydroruine
peganol


Plus any list of alkaloids found or suspected to be in Tetrapterys methistica, Alicia anisopetala, Banisteriopsis muricata.

This first post will be edited to add alkaloids and plants we need info on.

Thanks!


Edit: If you dont have access to scientific articles, go to this page and use the search bar to look for the articles, it connects you through different university proxies so you can download the articles. If you are in USA and when you click the link and it takes you to a scientific forum, its probably some ISP block, so you need to try to enter the webpage through some international proxy, and then it will work. This is what the page looks like.

I'm not sure is this is what you look for :

Banistenoside A :

Colorless solid;
UV (MeOH) λmax, nm: 226, 269 and 290;
IR (film) νmax, cm−1: 3382 (NH), 2920, 2850, 1804, 1752, 1631, 1225, 1037, 733;
HRESIMS m/z 367.1522 [MH+H2O-Glucosyl]+ (calcd. for C17H23N2O7, 367.1505);
529.2013 [MH+H2O]+ (calcd. for C23H33N2O12, 529.2033).

Source : http://www.sciencedirect...le/pii/S0378874109006862

Molecular structure :


UV Spectra :


Source : http://www.sciencedirect...le/pii/S0378874110001285

Please tell me if it useful for you, I'll try to help you as much as I can.

I found a list of alkaloids :

Tabernaemontana sananho
Coronaridine
Heyneanine
3-Hydroxycoronaridine
Ibogamine
Voacangine

Source : http://books.google.com....AV41_DJkXEGZ2Hf1Za56fEPs

poke around pubmed as well. a search on led me to this, may be of some use to you. its just the abstract, but if you could find the full text i imagine it would have lots of info you seek.

http://www.ncbi.nlm.nih.gov/pubmed/6371388

evil804, I've checked on this document as well, this is the same list of alkaloids.

Thanks a lot guys, this is exactly the kind of info im looking for I will check this out this weekend, and update the list with the info we already have, and with what we still need.

Peganum harmala :
harmine
harmaline
harmane
harmol
harmalol
tetrahydroharmine
vasicine (peganine)
deoxyvasicine (deoxypeganine)
vasicinone
deoxyvasicinone
pegamine
peganidine
isopeganidine
deoxypeganidine
dipegine
dipeginol
ruine
dihydroruine
peganol


Sources :

The usual list found on Internet :
http://en.wikipedia.org/wiki/Peganum_harmala (with many scientific sources)

A big list of alkaloid, but maybe with old name of alkloids :
http://94.102.48.117/mai...NjFkZWE4ODk2LnBkZg%3D%3D

Analytical data of dipegine and dipeginol :


Ruine: a glucosidic β-carboline from Peganum harmala


Deoxypeganidine — A new alkaloid from Peganum harmala


Info on peganine, peganol, deoxypeganine, peganidine, isopeganidine, deoxypeganidine, and pegamine

.....

Thanks once again, this is helping me save a lot of time!!

In the first post im already editing the lists to cross out the alkaloids we already have info, and added the name of alkaloids we still need to know. Anybody feel free to help out, and thanks a lot


Tabernaemontana sananho
Coronaridine

ibogamine​-18-carbo​xylic aci​d methyl​ ester
CAS: 467-77-6
338.44 g/mol
(More analytical info here but no mass spectra)



Peganum harmala
Dipegine (1)
Dipegine : C22H20N4O, mp 221-223oC (acetone). UV spectrum [CCl4, max , nm (log e)]: 226 (4.4, 277 (4.14), 305 (4.05), 317 (3.89) nm. IR spectrum (KBr, max, cm-1): 1590, 1620, 1660. 1H NMR (CDCl3, 400 MHz) and 13C NMR (CDCl3, 100 MHz) (Tables 1 and 2). EIMS, m/z (Irel): [M+] 356, 185 (3), 171 (100).


Dipeginol (1)
Dipeginol: C22H20N4O2 , mp 243oC. UV spectrum [CCl4, max , nm (log e)]: 225 (4.46), 276 (4.11), 303 (4.04), 317 (3.82) nm. IR spectrum (KBr, max, cm-1): 1580, 1630, 1680 cm-1. 1H NMR (CDCl3, 400 MHz) and 13C NMR (CDCl3, 100MHz) (Tables 1 and 2). EIMS, m/z: 201, 171.

Isolation of Dipeginol. (1) Total alkaloids were treated with acetone. The part of the alkaloid mixture that was insoluble in acetone (100 g) gave deoxypeganine perchlorate upon treatment with perchloric acid. The mother liquor was evaporated, basicified with NH4OH, and treated with ether. The solid left after evaporation of the ether was ground with
acetone. The part that was insoluble in acetone yielded peganine. The part that was soluble in acetone was evaporated and ground several times with acetone—ethylacetate (1:1). The remaining solid was crystallized from CH3OH. Yield 0.036 g of dipeginol as elongated prisms.


__________________________________

Sources : (1) Chemistry of Natural Compounds, Vol. 36, No. 6, 2000 ALKALOIDS OF Peganum harmala

From here





From attached:


I also added the tabernaemontana paper for kicks, although it does not appear to have any of the needed alkaloidal data.

NEW ORGANIC BASES FROM AMAZONIAN
BANISTERIOPSIS CAAPI
YOHEI HASHIMOTOa nd KAZUKO KAWANISHI
Institute of Phytochemistry, Kobe College of Pharmacy, Motoyamakita-machi, Higashinada-ku. Kobe, Japan

NEW ALKALOIDS FROM BANISTERIOPSIS CAAPI
YOHEI H~swron, and KAZUKO KAWANISM
Institute of Phytochemistry, Kobe College of Pharmacy, Motoyamakitamachi, Higashinada-ku, Kobe, Japan

MASS SPECTRA OF SELECTED BETA-CARBOLINES
[/?-9H-PYRIDO(3,4-b)IPdDOLES]
R. T. COUTTSR, . A. LOCOCKa nd G. W. A. SLYWKA
Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta,
Edmonton, Alberta, Canada.

JPGs + DOCs

Banistenoside B :

Colorless solid;
UV (MeOH) λmax, nm: 226, 269 and 290;
IR (film) νmax, cm−1: 3448 (NH), 3021, 2923, 2851, 1749, 1692, 1632, 1221, 1044, 757; HRESIMS m/z 367.1491 [MH+H2O-glucosyl]+ (calcd. for C17H23N2O7, 367.1505);
529.2028 [MH+H2O]+ (calcd. for C23H33N2O12, 529.2033).

Source : http://www.sciencedirect...le/pii/S0378874109006862

Molecular structure :


UV Spectra :


Source : http://www.sciencedirect...le/pii/S0378874110001285

Harmic acid methyl ester
C14H12N2O3
Mass 256.2567; Exact mass 256.084792260
IUPAC name: ethyl 7-methoxy-9H-pyrido[3,4-b]indole-1-carboxylate
Appearance: Light yellow needles from CHCl3
mp 118 °C (dec.)
MS: m/e 256 (68), 224 (10), 198 (100), 196 (73), 153 (19). M+ found at 256.087, calc'd at 256.085.
UV λmax (CHCl3): 256, 282, 323 nm
IR νmax (Nujol): 3398, 1693, 1635, 1625, 1600 and 1570 cm^-1
1H NMR: δ 3.89 (3-H, s: OMe), 4.04 (3-H, s: COOMe), 6.93 (1-H, q: J = 0.2 Hz; H-6), 7.31 (1-H, d: J = 2.2 Hz; H-8), 8.18 (1-H, q: J = 8.7 Hz; H-5), 8.26 (1-H, q: J = 4.5 Hz: H-4), 8.43 (1-H, q: J = 4.5 Hz: H-3), and 11.46 (1-H, b: indolic NH).



Harmalinic acid
C13H12N2O3
Mass 244.2460; Exact mass 244.084792260
IUPAC name: 7-methoxy-3H,4H,9H-pyrido[3,4-b]indole-1-carboxylic acid
Appearance: Yellow plates from MeOH
mp 224-225 °C (dec.)
MS: m/e 244 (82), 216 (93), 201 (29), 187 (39) and 159 (100). M+ found at 244.085*, calc'd at 244.085 (the paper actually says found at 224.085, but I'm confident that was a typo).
UV λmax (MeOH): 250 and 372 nm
IR νmax (Nujol): 3300, 1690, 1635, 1620, 1570 and 1525 cm^-1
1H NMR: δ 2.93-3.30 (2-H, m: H-3 or H-4), 3.38-3.76 (2-H, m: H-4 or H-3), 3.84 (3-H, s; OMe), 6.77 (1-H, q: J = 0.6 Hz; H-6), 6.92 (1-H, d: J = 2.1 Hz; H-8), 7.59 (1-H, q: J = 8.8 Hz; H-5), 8.72 (1-H, t: COOH) and 11.58 (1-H, b: indolic NH).



Data for both compounds from:

• Hashimoto, Y., and K. Kawanishi. 1975. "New organic bases from Amazonian Banisteriopsis caapi" Phytochemistry 14(7): 1633-1635.
  

Edit: I just saw that Ufostrahlen attached the relevant paper earlier in the thread. I'm going to assume that transcribing the data into searchable text is helpful and keep on doing it anyway.

Harmic Amide
C13H11N3O2
Mass 241.2453; Exact mass 241.085126611
IUPAC name: 7-methoxy-9H-pyrido[3,4-b]indole-1-carboxamide
Appearance: Needles from CHCl3 and MeOH
mp 226-227 °C (dec.)
MS: m/e 241 (l00), 224 (16), 196 (81), 181 (14) and 153 (23). M+ found at 241.086, calc'd at 241.085.
UV λmax (CHCl3): 255 (log ε 4.54), 279 (4.44) and 321 (4.35) nm
IR νmax (Nujol): 3420, 3390, 3200, 1700, 1635, 1595, 1570, and 1480 cm^-1
1H NMR: δ 63.87 (3-H, s, OMe), 6.87 (1-H, q, J = 0.5 Hz; H-6), 7.34 (1-H, d, J = 2.1 Hz; H-8), 8.12 (1-H, q, J = 8.6 Hz; H-5), 8.26 (l-H, q, J = 4.5 Hz; H-4), 8.34 (1-H, q, J = 4.5 Hz; H-3), 7.67 (2-H, b, CONH2) and 11.44 (1-H, b, indolic NH)
Present in Banisteriopsis caapi at 0.007%.


Acetyl Norharmine
C14H12N2O2
Mass 240.2573; Exact mass 240.089877638
IUPAC name: 1-{7-methoxy-9H-pyrido[3,4-b]indol-1-yl}ethan-1-one
Appearance: Light yellow needles from CHCl3
mp 224-225 °C (dec.)
MS: m/e 240 (l00), 225 (2), 212 (36), 198 (69), 197 (34), and 183 (16). M+ found at 240.089, calc'd at 240.090.
UV λmax (CHCl3): 260 (log ε 4.18), 289 (4.37), and 334 (4.02) nm
IR νmax (Nujol): 3370, 1670, 1630, 1595, 1585, and 1505 cm^-1
1H NMR: δ 2.78 (3-H, s, COMe), 3.83 (3-H, s, OMe), 6.92 (1-H, q, J = 6.5 Hz; H-6), 7.35 (1-H, d, J = 2.1 Hz; H-8), 8.12 (1-H, q, J = 8.2 Hz; H-5), 8.24 (1-H, q, J = 5 Hz; H-4), 8.44 (1-H, q, J = 5 Hz; H-3) and 11.65 (1-H, b, indolic NH)
Present in Banisteriopsis caapi at 0.0001%.


Ketotetrahydronorharmine
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-8) 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%.




Data for all three compounds from:

• Hashimoto, Y., and K. Kawanishi. 1976. "New alkaloids from Banisteriopsis caapi" Phytochemistry 15(10): 1559–1560.
  

Thanks a lot entropy, this is great!! And yeah, even if paper is posted already, it still saves me tons of work by opening each publication and searching through them and pasting stuff here, so what you're doing is a lot of help!

Now that we have almost all the caapi spectra, they dont seem to match the peaks in the caapi analysis thread.. Would be interesting if we could gather info on alkaloid in other related species (Banisteriopsis spp. , Tetrapterys spp, Alicia spp.). I just saw that cattle and other animals can get poisoned with some Tetrapterys spp plants, but I can't find alkaloid info, can anybody?

Some obscure iboga alkaloids

19(S)-Hydroxyibogamine (1): light yellowish oil;
[R]D-21° (c 0.16, CHCl3);
UV (EtOH) λmax (log ) 226 (4.2, 283 (3.66), 292 (3.62) nm;
IR (dry film) νmax 3355 cm-1;
1H NMR and 13C NMR data, see Tables 1 and 3;
EIMS m/z 296 [M]+(100), 281 (67), 278 (35), 251 (26), 195 (22), 162 (35), 152 (45), 138 (25), 136 (15), 122 (13);
HREIMS m/z 296.1898 (calcd for C19H24N2O, 296.1889).

19-epi-Isovoacristine (2): colorless oil;
[R]D -31° (c 0.05,CHCl3);
UV (EtOH) λmax (log ) 226 (4.31), 283 (3.64), 294 (3.61) nm;
IR (dry film) νmax 3533, 1723 cm-1;
1H NMR and 13C NMR data, see Tables 1 and 3; EIMS m/z 384 [M]+ (100), 366 (20), 339 (5), 325 (6), 244 (, 184 (1, 154 (15), 148 (5), 136 (35), 124 (20), 122 (13);
HREIMS m/z 384.2045 (calcd for C22H28N2O4, 384.2049).

Isovoacryptine (3): light yellowish oil;
[R]D +17° (c 0.85,CHCl3);
UV (EtOH) λmax (log ) 225 (4.25), 280 (3.8, 298 (3.97) nm;
IR (dry film) νmax 3382, 1725, 1711 cm-1;
1H NMR and 13C NMR data, see Tables 1 and 3; EIMS m/z 382 [M]+ (100), 339 (12), 323 (10), 244 (25), 184 (7), 160 (10), 136 (10), 124 (12), 122 (9);
HREIMS m/z 382.1890 (calcd for C22H26N2O4, 382.1893).

3R/S-Ethoxyheyneanine (4) (mixture 3R:3S ≈ 1:1): color-less oil;
UV (EtOH) λmax (log ) 225 (3.94), 285 (3.33), 292 (3.26) nm;
IR (dry film) νmax 3378, 3274, 1727 cm-1;
1H NMR and 13C NMR data, see Tables 2 and 3;
EIMS m/z 353 [M - OEt]+ (30), 352 [M - EtOH]+ (100), 337 (10), 308 (1, 270 (30), 229 (32), 214 (52), 182 (12), 154 (20), 138 (22), 136 (4), 124 (5), 122 (5);
HREIMS m/z 352.1823 [M - EtOH]+ (calcd for C21H24N2O3, 352.1787);
FABMS m/z 353 [M - OEt]+; HRFABMS m/z 353.1865 (calcd for C21H25N2O3, 353.1865);
APIMS m/z 385 (C22H28N2O4 + H).

3R/S-Ethoxy-19-epi-heyneanine (5) (mixture 3R:3S ≈1:1): colorless oil;
UV (EtOH) λmax (log ) 225 (3.91), 285 (3.29), 292 (3.23) nm;
IR (dry film) νmax 3378, 1728 cm-1;
1H NMR and 13C NMR data, see Tables 2 and 3;
EIMS m/z 353 [M -OEt]+ (45), 352 [M - EtOH]+ (100), 337 (34), 308 (20), 270 (30), 229 (24), 214 (5, 182 (11), 154 (22), 138 (16), 136 (5),
124 (10), 122 (10); HREIMS m/z 352.1772 [M - EtOH]+ (calcd
for C21H24N2O3, 352.1787); FABMS m/z 353 [M - OEt]+;
HRFABMS m/z 353.1913 (calcd for C21H25N2O3, 353.1865);
APIMS m/z 385 (C22H28N2O4 + H).

3R/S-Ethoxycoronaridine16 (mixture 3R:3S ≈ 2:1): light yellowish oil;
UV (EtOH) λmax (log ) 224 (4.41), 285 (3.81), 292 (3.76) nm;
IR (dry film) νmax 3375, 1728 cm-1;
1H NMR and 13C NMR data, see Tables 1 and 3;
EIMS m/z 337 [M - OEt]+(80), 336 [M - EtOH]+ (100), 323 (25), 293 (20), 277 (20), 154(4, 136 (40), 124 (35), 122 (30);
FABMS m/z 337 [M - OEt]+;
APIMS m/z 369 (C22H28N2O3 + H).

From -
Five New Iboga Alkaloids from Tabernaemontana corymbosa
Toh-Seok Kam* and Kooi-Mow Sim
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia

File Attached :]
*Still editing to add more information, posting to save work progress*

Crap it won't let me post an attachment in an edit... anyways.(sorry to wreck the flow)

Here is the publication listing the information for the post above

as well as a C13-NMR paper on iboga alkaloids(probably not that useful but why not)

C13 - N M R . Spectroscopy of Naturally Occurring Substances. XLV. Iboga Alkaloids
by Ernest Wenker, David W. Cochran, Hugo E. Gottlieb and Edward W. Hagaman
Department of Chemistry, Indiana University, Bloomington, Indiana 47401, U.S.A.


Also in this link - https://www.dmt-nexus.me...aspx?g=posts&t=27205
Benzyme makes mention of NMR data for some alkaloids available in some of the literature described.

Sorry to be spamming all disorderly but I keep finding more.

Taken from "The alkaloids : Chemistry and Pharmacology" Volume number 29 on google books.

Vasicine page 111
Vasicinone page 114

There are references in this book to probably find a lot of the missing keys you need.

So hope this is appropriate in this space but I'm very curious about a couple of things:
First the profile of complex sugars in the vines themselves. I know they're not alkaloids but my experience with the profound healing effect of medicional mushrooms has me curious of the sugars in the vine, especially given the sweet flavor of a well made brew.

Secondly im not seeing any analysis of the leaves of Alecia, im here in Peru to make a brew of Chali, Alecia, Chacruna leaf with caapi vine at the instruction if beings in the Astral. They say it (and brews like it I'm sure) are the future of Ayahuasca, the next step in the evolution of this work. So in that light I am interested in tryptamine profiles if these plants. The other aspect of this mission is to collect seeds for plantations in Brasil which I am working to establish under a nonprofit foundation to deliver medicine on a donation basis, to ensure future supply of this now niche spectra of lianas and to work to conserve wild populations.

Anyway, I'm here on the ground so if I can be of any help please let me know. I will put in some research time as I am able but my laptop doesnt charge here 🤣.
I will for sure be taking good photos of leaf, vine, and seed wherever possible to ensure most accurate ID.

Also I'll be very interested in getting some samples tested, especially of leaf material. If there is anything you can tell me about how to prepare it for testing I will do my best with what is available.
Also curious about genetic testing of these samples... what is needed and what is on file, from what regions etc. I'll be in the Pucallpa area this time, later I will collect genetics from Ecuador as well.

Thanks all for the good work, this is all more important than we can currently know.
This is very exciting territory these lianas, a lifetime study and with a lot of depth on the material study side and the Astral realms as well. Grateful to have such magical allies, plant and human alike!
Bless your works and your lives!

Presumably you mean Alicia anisopetala. Try searching with that name instead.


Interesting comment about the saccharides (complex sugars) although oligo- and polysaccharides won't necessarily have a sweet taste. The structure of banistenosides A and B pictured above are to some degree noteworthy in this respect.