Psycholeine

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MedKoo CAT#: 412254

CAS#: 144424-79-3

Description: Psycholeine is isolated from the tropical plant Psychotria oleoides; exhibits somatostatin antagonistic activity on growth hormone secretion.

Chemical Structure

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Psycholeine
CAS# 144424-79-3
Instruction

Theoretical Analysis

MedKoo Cat#: 412254
Name: Psycholeine
CAS#: 144424-79-3
Chemical Formula: C44H50N8
Exact Mass: 690.42
Molecular Weight: 690.940
Elemental Analysis: C, 76.49; H, 7.29; N, 16.22

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Psycholeine

IUPAC/Chemical Name: (5S,11R)-13,16-dimethyl-1,7-bis((3aR,8aR)-1-methyl-2,3,8,8a-tetrahydropyrrolo[2,3-b]indol-3a(1H)-yl)-5,6,11,12-tetrahydro-5,10b:11,4b-bis(epiminoethano)dibenzo[c,h][2,6]naphthyridine

InChi Key: HEDIOFZXUDVGEU-WATQSORBSA-N

InChi Code: InChI=1S/C44H50N8/c1-26-25-45-37-43-21-24-52(4)40(49-35-29(13-9-15-31(35)43)41-19-22-50(2)38(41)46-33-17-7-5-11-27(33)41)44(26,43)32-16-10-14-30(36(32)48-37)42-20-23-51(3)39(42)47-34-18-8-6-12-28(34)42/h5-18,26,37-40,45-49H,19-25H2,1-4H3/t26?,37-,38+,39+,40+,41+,42+,43?,44?/m0/s1

SMILES Code: CC1CN[C@H]2Nc3c(C14[C@@H]5Nc6c(C24CCN5C)cccc6[C@]78CCN([C@H]7Nc9c8cccc9)C)cccc3[C@]%10%11CCN([C@H]%10Nc%12c%11cccc%12)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 690.94 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Lindovska P, Movassaghi M. Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines. J Am Chem Soc. 2017 Dec 6;139(48):17590-17596. doi: 10.1021/jacs.7b09929. Epub 2017 Nov 20. PMID: 29058431; PMCID: PMC5733798.

2: Juster RP, Sindi S, Marin MF, Perna A, Hashemi A, Pruessner JC, Lupien SJ. A clinical allostatic load index is associated with burnout symptoms and hypocortisolemic profiles in healthy workers. Psychoneuroendocrinology. 2011 Jul;36(6):797-805. doi: 10.1016/j.psyneuen.2010.11.001. Epub 2010 Dec 3. PMID: 21129851.

3: Lebsack AD, Link JT, Overman LE, Stearns BA. Enantioselective total synthesis of quadrigemine C and psycholeine. J Am Chem Soc. 2002 Aug 7;124(31):9008-9. doi: 10.1021/ja0267425. PMID: 12148978.

4: Rasolonjanahary R, Sévenet T, Guéritte Voegelein F, Kordon C. Psycholeine, a natural alkaloid extracted from Psychotria oleoides, acts as a weak antagonist of somatostatin. Eur J Pharmacol. 1995 Oct 4;285(1):19-23. doi: 10.1016/0014-2999(95)00345-l. PMID: 8846807.

5: Guéritte-Voegelein F, Sévenet T, Pusset J, Adeline MT, Gillet B, Beloeil JC, Guénard D, Potier P, Rasolonjanahary R, Kordon C. Alkaloids from Psychotria oleoides with activity on growth hormone release. J Nat Prod. 1992 Jul;55(7):923-30. doi: 10.1021/np50085a012. PMID: 1402957.

6: Sévenet T. Looking for new drugs: what criteria? J Ethnopharmacol. 1991 Apr;32(1-3):83-90. doi: 10.1016/0378-8741(91)90106-n. PMID: 1881171.