Synonym
Phencyclone; NSC101867; NSC 101867; NSC-101867;
IUPAC/Chemical Name
1,3-diphenyl-2H-cyclopenta[l]phenanthren-2-one
InChi Key
MNSDGJFEKUKHGO-UHFFFAOYSA-N
InChi Code
1S/C29H18O/c30-29-25(19-11-3-1-4-12-19)27-23-17-9-7-15-21(23)22-16-8-10-18-24(22)28(27)26(29)20-13-5-2-6-14-20/h1-18H
SMILES Code
O=C1C(=C2C(=C1C3=CC=CC=C3)C4=CC=CC=C4C5=CC=CC=C25)C6=CC=CC=C6
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
382.46
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: Roth AD, Thamattoor DM. Formation and Rearrangement of a Congested Spiropentane from the Trapping of Dibenzonorcarynyliden(e/oid) by Phencyclone. Org Lett. 2024 May 10;26(18):3840-3843. doi: 10.1021/acs.orglett.4c01001. Epub 2024 Apr 26. PMID: 38669627; PMCID: PMC11091884.
2: Callahan R, Prip R, Shariff N, Sklyut O, Rothchild R, Bynum K. 1H and 13C nuclear magnetic resonance studies of the hindered phencyclone adducts of some smaller branched N-alkyl maleimides: rigorous aryl proton assignments with high- resolution two-dimensional (COSY45) spectroscopy, and anisotropic shielding effects and ab initio geometry optimizations. Appl Spectrosc. 2005 Mar;59(3):354-65. doi: 10.1366/0003702053585426. PMID: 15901318.
3: Rosmarion K, Tokhunts R, Rothchild R. Diels-alder adducts of 3,6-dibromophencyclone with symmetrical 1,4-disubstituted-cis-2-butenes: comparisons with the adduct of phencyclone and N-benzylmaleimide, and one- dimensional and two-dimensional nuclear magnetic resonance studies and ab initio structure calculations. Appl Spectrosc. 2005 Mar;59(3):366-75. doi: 10.1366/0003702053585408. PMID: 15901319.
4: Yamaguchi K, Eto M, Harano K. Formation mechanism of triketo cage compounds from reaction of phencyclone with benzoquinones: cascade reaction of intermolecular [4+2]π and intramolecular [2+2]π cycloadditions. Chem Pharm Bull (Tokyo). 2013;61(10):1065-70. doi: 10.1248/cpb.c13-00240. Epub 2013 Aug 3. PMID: 23912634.
5: Yoshitake Y, Misaka J, Abe M, Yamasaki M, Eto M, Harano K. Carboxylic acid clathrate hosts of Diels-Alder adducts of phencyclone and 2-alkenoic acids. Role of bidentate C-H ... O hydrogen bonds between the phenanthrene and carbonyl groups in host-host networks. Org Biomol Chem. 2003 Apr 7;1(7):1240-9. doi: 10.1039/b212129h. PMID: 12926401.
6: Rosmarion K, Rothchild R. Diels-alder adducts of 3,6-dibromophencyclone with short-chain N-n-alkylmaleimides: 1H and 13C nuclear magnetic resonance studies of hindered rotations and magnetic anisotropy, and ab initio calculations for optimized structures. Appl Spectrosc. 2005 Mar;59(3):376-84. doi: 10.1366/0003702053585453. PMID: 15901320.
7: Prati L, Mancinelli M, Ciogli A, Mazzanti A. Tetrasubstituted cyclopentadienones as suitable enantiopure ligands with axial chirality. Org Biomol Chem. 2017 Oct 25;15(41):8720-8728. doi: 10.1039/c7ob01455d. PMID: 28932855.
8: Tomita N, Murata M, Watanabe H, Ichikawa T, Washiyama K, Kumanishi T, Takahashi Y. The effects of DCG-IV and L-CCG-1 upon phencyclidine (PCP)-induced locomotion and behavioral changes in mice. Ann N Y Acad Sci. 2000 Sep;914:284-91. doi: 10.1111/j.1749-6632.2000.tb05203.x. PMID: 11085328.
9: Hashimoto K, Fujita Y, Ishima T, Chaki S, Iyo M. Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of the glycine transporter-1 inhibitor NFPS and D-serine. Eur Neuropsychopharmacol. 2008 Jun;18(6):414-21. doi: 10.1016/j.euroneuro.2007.07.009. Epub 2007 Sep 4. PMID: 17804206.
10: Pauloehrl T, Welle A, Bruns M, Linkert K, Börner HG, Bastmeyer M, Delaittre G, Barner-Kowollik C. Spatially controlled surface immobilization of nonmodified peptides. Angew Chem Int Ed Engl. 2013 Sep 9;52(37):9714-8. doi: 10.1002/anie.201302040. Epub 2013 Jul 24. PMID: 23893777.
