1438-62-6

Basic information

• Product Name: 1-Naphthalenepropanol,.alp
• Synonyms: 1-Naphthalenepropanol,.alp;(+)-13-epi-Manool;(13S)-Labda-8(17),14-dien-13-ol;(1S,αS,4aα)-α-Ethenyldecahydro-α,5,5,8aβ-tetramethyl-2-methylene-1β-naphthalene-1-propanol;[13S,(+)]-Labda-8(17),14-dien-13-ol;13-Epimanool;epi-13-Manool
• CAS NO: 1438-62-6
• Molecular Formula: C₂₀H₃₄O
• Molecular Weight: 290.48
• Mol File: 1438-62-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 35-38 °C
• Boiling Point: 368.2±11.0 °C(Predicted)
• Appearance: /
• Density: 0.93±0.1 g/cm3(Predicted)
• PKA: 14.47±0.29(Predicted)
• CAS DataBase Reference: 1-Naphthalenepropanol,.alp(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenepropanol,.alp(1438-62-6)
• EPA Substance Registry System: 1-Naphthalenepropanol,.alp(1438-62-6)

Safety Data

• Hazardous Substances Data: 1438-62-6(Hazardous Substances Data)

Usage

General Description

1-Naphthalenepropanol, also known as α-naphthylisopropylamine or alp, is a chemical compound that belongs to the family of monoamine neurotransmitter reuptake inhibitors. It is a psychoactive substance that has been used as a recreational drug and is structurally related to amphetamine, with similar stimulant and empathogenic effects. Alp has been found to act as a releasing agent of serotonin, norepinephrine, and dopamine, leading to increased levels of these neurotransmitters in the brain. Its effects include euphoria, increased sociability, and feelings of empathy, but it has also been associated with negative side effects such as anxiety, paranoia, and insomnia. Alp is considered to have a high potential for abuse and addiction and is classified as a controlled substance in many countries.

InChI:InChI=1S/C20H34O/c1-7-19(5,21)14-11-16-15(2)9-10-17-18(3,4)12-8-13-20(16,17)6/h7,16-17,21H,1-2,8-14H2,3-6H3/t16-,17-,19?,20+/m1/s1

Upstream product

• 10483-51-9 labda-8⁽¹⁷⁾,13-diene 
• 10395-41-2 labda-8⁽¹⁷⁾,13-diene 
• 6699-20-3 (E,E,E)-geranylgeranyl diphosphate 
• 131889-10-6 8⁽¹⁷⁾-labdadien-3R,13R-diol 
• 515-03-7 sclareol 
• 147802-35-5 3-oxo-8⁽¹⁷⁾-labdadien-13R-ol 
• 40768-86-3 14,15-dihydromanool 
• 596-85-0 epimanool 

Downstream Products

• 51371-15-4 8β-hydroxypodocarpan-13-one 
• 596-84-9 manoyl oxide 
• 10266-75-8 4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one 
• 74285-89-5 13-hydroxy-7-oxo-13-deisopropyldehydroabietane 
• 14506-67-3 15,16,17-trinorlabdane-8,13-dione 
• 14022-44-7 podocarp-8⁽¹⁴⁾-en-13-one 
• 74285-88-4 13-methoxy-7-oxo-13-deisopropyldehydroabietane 
• 100761-24-8 podocarp-8(14)-en-12α-hydroxy-13-one 
• 157318-11-1 podocarpa-8,11,13-trien-12,13-diol 
• 1309762-26-2 podocarp-8(14)-en-13-one-12α-yl acetate 
• 1309762-25-1 13-hydroxypodocarpa-6,8,11,13-tetraene 
• 69748-52-3 (+)-(5S,10S)-13-hydroxypodocarpa-8,11,13-triene 
• 1020186-21-3 C₂₈H₄₂O₂ 
• 2584-47-6 1,4-dimethylquinolin-2(1H)-one 

Relevant articles and documents

Substrate specificity of Rv3378c, an enzyme from Mycobacterium tuberculosis, and the inhibitory activity of the bicyclic diterpenoids against macrophage phagocytosis

The Rv3378c gene product from Mycobacterium tuberculosis encodes a diterpene synthase to produce tuberculosinol (3), 13R-isotuberculosinol (4a), and 13S-isotuberculosinol (4b) from tuberculosinyl diphosphate (2). The product distribution ratios are 1:1 for 3 to 4 and 1:3 for 4a to 4b. The substrate specificity of the Rv3378c-encoded enzyme was examined. The 3 labdadienyl diphosphates, copalyl diphosphate (CDP) (7), ent-CDP (8), and syn-CDP (9), underwent the conversion reaction, with good yields (67-78%). Copalol (23) and manool (24) were produced from 7, ent-copalol (25) and ent-manool (26) from 8, and syn-copalol (27) and vitexifolin A (28) from 9. The ratio of 23 to 24 was 40:27, that of 25:26 was 22:50, and that of 27:28 was 16:62. Analysis on a GC-MS chromatograph equipped with a chiral column revealed that 24, 26, and 28 consisted of a mixture of 13R- (a) and 13S-stereoisomers (b) in the following ratio: ca. 1:1 for 24a to 24b, ca. 1:5 for 26a to 26b, and ca. 1:19 for 28a to 28b. The structures of these products indicate that the reactions of the 3 CDPs proceeded in the same fashion as that of 2. This is the first report on the enzymatic synthesis of natural diterpenes manool, ent-manool, and vitexifolin A. Both Rv3377c and Rv3378c genes are found in virulent Mycobacterium species, but not in avirulent species. We found that 3 and 4 inhibited the phagocytosis of opsonized zymosan particles by human macrophage-like cells. Interestingly, the inhibitory activity was synergistically increased by the coexistence of 3 and 4b. Other labdane-related diterpenes, 13-16 and 23-28, had little or no inhibitory activity. This synergistic inhibition by 3 and 4 may provide further advantage to the impairment of phagocyte function, which might contribute to pathogenicity of M. tuberculosis.

TERPENOIDS AND STEROLS FROM THE WOOD OF ABIES PINSAPO

From the neutral fraction of the hexane extract of the wood of Abies pinsapo 11 sesquiterpenoids, seven diterpenoids, three triterpenoids and two sterols have been identified.Three of them are new natural products: 3β-hydroxy-13-epimanool, (23R,25R)-3α-methoxy-9,19-cyclo-9β-lanostan-26,23-olide and (22S)-5α-ergostane-3α,22-diol.Their structure were established by spectroscopic methods and chemical correlations. Key words: Abies pinsapo; Pinaceae; wood; labdane diterpenoids; cyclolanostanolides; sterols.

Photosensitized Oxygenation of Labda-8(17),12-diene, Labda-8(17),13-diene, and the Biformenes. Synthesis of Pumiloxide

Reactions of the title compounds with singlet oxygen were studied.In labda-8(17),12-diene (2; 7:3 mixture of E and Z isomers), syn addition leading to 7 (58percent) was predominant.Smaller amounts of 8 (20percent) by syn addition to (E)-2 or anti addition to (Z)-2, 9 (5percent), 10 (2,5percent), and 11(1.5percent) were also formed. (E)-Labda-8(17),13-diene ((E)-3) gave 29percent 12 and 40percent 13 by syn addition, whereas (Z)-3 gave 57percent 12 by syn addition and 19percent 13 by anti addition.In trans-biformene (5) syn attack at C-12 to give 15 (27percent), 16 (10percent), 18 (12percent), and 19 (4percent) was greatly preferred to syn attack at C-13 to give 17 (6percent).In cis-biformene (6) syn attack at C-13 to give 17 (39percent) predominated slightly over anti attack at C-12 to give 15 (13percent), 16 (8percent), 18 (4percent), and 19 (4percent).Diels-Alder reactions with singlet oxygen leading to epidioxides 20 and 21 were relatively unimportant (7percent from 5, 5percent from 6).The epidioxides were converted to the naturally occurring furanolabdane pumiloxide (22).