5001-21-8

Basic information

• Product Name: Ormosanine
• Synonyms: Ormosanine;Piptamine
• CAS NO: 5001-21-8
• Molecular Formula: C20H35N3
• Molecular Weight: 317.512
• Mol File: 5001-21-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 404.8°Cat760mmHg
• Flash Point: 193.7°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 9.18E-07mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: Ormosanine(CAS DataBase Reference)
• NIST Chemistry Reference: Ormosanine(5001-21-8)
• EPA Substance Registry System: Ormosanine(5001-21-8)

Safety Data

• Hazardous Substances Data: 5001-21-8(Hazardous Substances Data)

Usage

Description

Isolated from various Orrnosia species, this optically inactive base has physical and chemical characteristics very like those of piptamine (q.v.) with which it may be identical. The dihydriodide forms colourless prisms from H20, m.p. 249°C (dec.). Heating with formaldehyde furnishes Jamine (q.v.).

References

Konovalova, Diskina, Rabinovitch.,J. Gen. Chern., USSR, 21,773 (1951)Lloyd, Horning.,J. Arner. Chern. Soc., SO, 1506 (195S)Naegeli, Wildman, Lloyd., Tetrahedron Lett., 2L69 (1963)Naegeli, Wildman, Lloyd., Tetrahedron Lett., 2L69 (1963)Hassall, Wilson., J. Chern. Soc., 2657 (1964)

InChI:InChI=1/C20H35N3/c1-3-9-21-18(8-1)20-13-16(12-15-6-5-10-22-19(15)20)17-7-2-4-11-23(17)14-20/h15-19,21-22H,1-14H2/t15-,16+,17+,18+,19+,20-/m0/s1

Upstream product

• 1361-42-8 (-)-podopetaline 
• 2448-27-3 C₂₀H₃₃N₃ 

Relevant articles and documents

Alkaloids of Templetonia retusa. Chemistry, Structure and Absolute Configuration of (-)-Templetine

(-)-Cytisine, (+)-lupanine, (-)-anagyrine, (+/-)-piptanthine and (-)-templetine have been isolated from Templetonia retusa (Vent.) R.Br.The absolute crystal structures of the trihydrochloride dihydrate and the isomorphous trihydrobromide dihydrate of (-)-templetine have both been determined by single-crystal X-ray diffraction; diffractometer data at 295 K were refined by least-squares techniques to residuals of 0.045 and 0.031, respectively, for 2351 and 1948 'observed' reflections.Crystals of the trihydrochloride are orthorhombic P212121, a 8.830(4), b 14.201(6) c 19.122(12) Angstroem, Z 4.Crystals of the trihydrobromide are isomorphous, a 9.081(3), b 14.578(2), c 19.197(11) Angstroem, Z 4.The absolute structure (1) of (-)-templetine has led to the absolute structure of its dehydrogenation product (-)-dehydropiptanthine perchlorate (7) which, in turn, has allowed the absolute structures of (-)-ormosanine (6), (+)-piptanthine (4) and (-)-panamine (9) to be defined. (-)-Templetine (1) reacts with formaldehyde to form homotempletine (12) and with carbon disulfide to yield the thiourea (13).Treatment of either (12) or (13) with W-1 Raney nickel followed by perchloric acid has yielded the diperchlorate (15).The X-ray crystal structure of the diperchlorate (15) has also been determined: diffractometer data at 295 K were refined by least-squares techniques to a residual of 0.056 (1312 'observed' reflections).Crystals of the diperchlorate (15) are orthorhombic, P212121, a 18.636(5), b 12.569(6), c 10.403(4) Angstroem, Z 4.