Synonym
Setoclavine; Setoclavin;
IUPAC/Chemical Name
(6aR,9S)-7,9-dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-ol
InChi Key
BGVUWLLRNRBDAY-ZBFHGGJFSA-N
InChi Code
1S/C16H18N2O/c1-16(19)7-12-11-4-3-5-13-15(11)10(8-17-13)6-14(12)18(2)9-16/h3-5,7-8,14,17,19H,6,9H2,1-2H3/t14-,16+/m1/s1
SMILES Code
[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@](C)(O)CN2C
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
254.33
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.
| 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 |
1: Liras S, Lynch CL, Fryer AM, Vu BT, Martin SF. Applications of vinylogous Mannich reactions. Total syntheses of the Ergot alkaloids rugulovasines A and B and setoclavine. J Am Chem Soc. 2001 Jun 27;123(25):5918-24. doi: 10.1021/ja010577w. PMID: 11414824.
2: Bajwa RS, Anderson JA. Conversion of agroclavine to setoclavine and isosetoclavine in cell-free extracts from Claviceps sp. SD 58 and in a thioglycolate-iron (II) system. J Pharm Sci. 1975 Feb;64(2):343-4. doi: 10.1002/jps.2600640237. PMID: 236378.
3: Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW. Identification of legal highs--ergot alkaloid patterns in two Argyreia nervosa products. Forensic Sci Int. 2014 Sep;242:62-71. doi: 10.1016/j.forsciint.2014.06.025. Epub 2014 Jun 30. PMID: 25036782.
4: Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW. Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high. Forensic Sci Int. 2015 Apr;249:281-93. doi: 10.1016/j.forsciint.2015.02.011. Epub 2015 Feb 19. PMID: 25747328.
5: Coyle CM, Cheng JZ, O'Connor SE, Panaccione DG. An old yellow enzyme gene controls the branch point between Aspergillus fumigatus and Claviceps purpurea ergot alkaloid pathways. Appl Environ Microbiol. 2010 Jun;76(12):3898-903. doi: 10.1128/AEM.02914-09. Epub 2010 Apr 30. PMID: 20435769; PMCID: PMC2893504.
