Psychotridine
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-05255 |
| CAS | 52617-25-1 |
| Molecular Weight | 863.15 |
| Molecular Formula | C55H62N10 |
| Purity | >95% by HPLC |
Online Inquiry
Description
Psychotridine is an alkaloid that has been found in P. forsteriana and has diverse biological activities. It inhibits ADP-, collagen-, or thrombin-induced aggregation of washed isolated human platelets.
Specification
| Synonyms | Isopsychotridine; 1,1',1'',1''',1''''-Pentamethyl-2,2',2'',2''',2'''',3,3',3'',3''',3'''',8,8',8'',8''',8'''',8a,8a',8a'',8a''',8a''''-icosahydro-1H,1'H,1''H,1'''H,1''''H-3a,7':3a',3a'':7'',3a''':7''',3a''''-quinquepyr rolo[2,3-b]indole; Stereoisomer of 2,2',2'',2''',2'''',3,3',3'',3''',3'''',8,8',8'',8''',8'''',8a,8'a,8' 'a,8'''a,8''''a-eicosahydro-1,1',1'',1''',1''''-pentamethyl-3a(1H),7':3'a,3''a(1'H,1''H):7'',3'''a(1'''H):7''',3''''a(1''''H)-quinquepyrrolo[2,3-b]indole |
| Storage | Store at -20°C |
| IUPAC Name | 3-methyl-5,8b-bis[3-methyl-5-(3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-yl)-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-yl]-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole |
| Canonical SMILES | CN1CCC2(C1NC3=CC=CC=C32)C4=C5C(=CC=C4)C6(CCN(C6N5)C)C7=C8C(=CC=C7)C9(CCN(C9N8)C)C12CCN(C1NC1=C(C=CC=C21)C12CCN(C1NC1=CC=CC=C21)C)C |
| InChI | InChI=1S/C55H62N10/c1-61-28-23-51(33-13-6-8-21-41(33)56-46(51)61)35-15-10-16-36-43(35)58-48-53(36,25-30-63(48)3)38-18-12-20-40-45(38)60-50-55(40,27-32-65(50)5)54-26-31-64(4)49(54)59-44-37(17-11-19-39(44)54)52-24-29-62(2)47(52)57-42-22-9-7-14-34(42)52/h6-22,46-50,56-60H,23-32H2,1-5H3 |
| InChI Key | DVJSMVZSIBHXAO-UHFFFAOYSA-N |
Properties
| Appearance | Solid |
| Density | 1.286 g/cm3 |
| Solubility | Soluble in DMSO, Methanol |
Reference Reading
1. Involvement of NMDA receptors in the analgesic properties of psychotridine
T A Amador, L Verotta, D S Nunes, E Elisabetsky Phytomedicine. 2001 May;8(3):202-6. doi: 10.1078/0944-7113-00025.
We have previously reported that the alkaloid extract of Psychotria colorata (Willd. ex R. & S.) Muell. Arg., had marked dose-dependent, opioid-like activity. Phytochemical analyses of P. colorata flowers and leaves identified several pyrrolidinoindoline alkaloids, including psychotridine. To further investigate the activity and mechanism of action of Psychotria alkaloids, we studied the effects of psychotridine on thermal and chemical models of analgesia. In the tail-flick model, psychotridine presents a dose-dependent analgesic effect; the effect is not reversed by prior treatment with naloxone. Psychotridine dose-dependently decreased capsaicin-induced pain. Performance in the rotarod test showed that psychotridine does not induce motor deficits at doses effective in analgesia models. Psychotridine inhibited [3H]MK-801 (dizocilpine) binding to cortex membranes in a dose-dependent manner. Binding is completely abolished at 300 nM. The data rule out opioid activity, and the inhibition of capsaicin-induced pain and of radioligand binding strongly suggest the participation of NMDA receptors in psychotridine-induced analgesia.
2. Total Synthesis and Stereochemical Assignment of (-)-Psychotridine
Tony Z Scott, Vinicius F Armelin, Mohammad Movassaghi Org Lett. 2022 Mar 25;24(11):2160-2164. doi: 10.1021/acs.orglett.2c00448. Epub 2022 Mar 17.
We report the first enantioselective total synthesis and stereochemical assignment of (-)-psychotridine. The application of our diazene-directed assembly of enantiomerically enriched cyclotryptamines afforded a highly convergent synthesis of the pentameric alkaloid, allowing its detailed structural assignment. Highlights of the synthesis include the introduction of four quaternary stereocenters with complete stereochemical control in a single step via the photoextrusion of three molecules of dinitrogen from an advanced intermediate and metal-catalyzed C-H amination reactions in challenging settings.
3. Pyrrolidinoindoline alkaloids from Psychotria oleoides and Psychotria lyciiflora
V Jannic, F Guéritte, O Laprévote, L Serani, M T Martin, T Sévenet, P Potier J Nat Prod. 1999 Jun;62(6):838-43. doi: 10.1021/np9805387.
The chemical study of two Rubiaceae from New Caledonia, Psychotria lyciiflora and Psychotria oleoides, led to the isolation of several pyrrolidinoindoline alkaloids. Two dimers, the known meso-chimonanthine (9) and the new Nb-desmethyl-meso-chimonanthine (5), and a known trimer, hodgkinsine (1), have been isolated from P. lyciiflora. Hodgkinsine (1), quadrigemine C (2), isopsychotridine B (3), psychotridine (4), and three new alkaloids, quadrigemine I (6), oleoidine (7), and caledonine (8), have been isolated from P. oleoides. Structural assignments of the compounds were based on mass spectra analysis and 2D NMR experiments. A tentative stereochemical determination is made from 2D NMR experiments, circular dichroism study and chemical correlations. Some of these compounds are functional antagonists of somatostatine (SRIH).
Recommended Products
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
