Substituted 4,7-dihydroindoles. Remers, William A.; Weiss, Martin J. (American Cyanamid Co.). U.S. (1969), 4 pp. CODEN: USXXAMPatent US3444174 (http://l2.espacenet.com/dips/viewer?PN=US3444174&CY=gb&LG=en&DB=EPD)
19690513 Patent written in English. Application: US 66-584355 19661005. CAN 72:66809 AN 1970:66809 CAPLUS
Patent Family Information
Patent No. Kind Date Application No. Date
US 3444174 A 19690513 US 1966-584355 19661005
Priority Application
US 1966-584355 19661005
Abstract
Substituted 4,7-dihydroindoles were prepd. from the corresponding indoles by treatment with an alkali metal or alk. earth metal in liq. NH3 in the presence of an alc. For example, a mixt. of 2.4 g 5-methoxytryptamine, 50 ml Et2O, and 500 ml liq. NH3 was treated with 4 g Li wire. After 1 hr, MeOH was added until disappearance of the blue color. Evapn. of NH3 and extn. of the residue gave 1.27 g 4,7-dihydro-5-methoxytryptamine, m. 100-14°. Other 4,7-dihydroindoles prepd. were 4,7-dihydro-2,7-dimethyl-5-methoxy-N,N-dimethyltryptamine, m. 80-3°; 4,7-dihydro-5-methoxy-N,N-dimethyltryptamine, m. 91-3°; 4,7-dihydro-2,7-dimethyl-5-methoxy-N,N-pentamethyl-enetryptamine; 4,7-dihydro-5-methoxyindole, m. 65-8°; 4,7-dihydro-6-methoxyindole; 4,7-dihydro-5-methoxy-1-methyl-N,-N-dimethyltryptamine; 4,7-dihydro-a-ethyltryptamine, m. 76-9°. These compds. have analgesic and central nervous system depressant properties.
Synthesis and analgesic activity of N-(N-acetyl-L-amino-acyl)-5-methoxytryptamines. Dongmei, Han; Chao, Wang; Ming, Zhao; Shiqi, Peng. College of Pharmaceutical Sciences, Beijing Medical University, Beijing, Peop. Rep. China. Preparative Biochemistry & Biotechnology (2000), 30(1), 39-47. CODEN: PBBIF4 ISSN: 1082-6068. Journal written in English. CAN 132:322109 AN 2000:138442 CAPLUS
Abstract
5-Methoxytryptamine was acylated with N-acetyl-L-amino acids to give N-(N-acetyl-L-amino acyl)-5-methoxytryptamines which were evaluated for analgesic by the tail flick test. Among the six compds. that were prepd, the analgesic potencies of N-(N-acetyltryptophanyl)-5-methoxytryptamine and N-(N-acetylglycyl)-5-methoxytryptamine were much more potent than that of melatonin.
Synthesis and analgesic activity of N,N'-dicarbonyltryptamines. Dongmei, Han; Chao, Wang; Ming, Zhao; Shiqi, Peng. College of Pharmaceutical Sciences, Beijing Medical University, Beijing, Peop. Rep. China. Preparative Biochemistry & Biotechnology (2000), 30(3), 231-240. CODEN: PBBIF4 ISSN: 1082-6068. Journal written in English. CAN 133:252248 AN 2000:520139 CAPLUS
Abstract
5-Methoxytryptamine and L-tryptophan Me ester were acylated with malonic acid, di-Me malonate, or succinic anhydride to produce the corresponding N,N'-dicarbonyltryptamine derivs. The analgesic activity was evaluated by the tail flick test. All of the compds. exhibited desirable analgesic potency. This result is consistent with that of N-(N-acetyl-L-tryptophanyl)-5-methoxytryptamine and confirmed that introducing substituted tryptamine into the amide chain of melatonin does enhance analgesic potency.
Patent US3444174 (http://l2.espacenet.com/dips/viewer?PN=US3444174&CY=gb&LG=en&DB=EPD)
, example 1, I wonder what would be created if something easier to work with, such as diethylamine, is used in place of the ammonia? Maybe it would have analgesic properties?Medline (PMID=86142792) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=86142792&dopt=Abstract)
Medline (PMID=6293841) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=6293841&dopt=Abstract)
Medline (PMID=7092918) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=7092918&dopt=Abstract)
Medline (PMID=2858526) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=2858526&dopt=Abstract)
Medline (PMID=91068238) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=91068238&dopt=Abstract)
it kills brain cells!Medline (PMID=91334549) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=91334549&dopt=Abstract)
Medline (PMID=82231462) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=82231462&dopt=Abstract)
Medline (PMID=89211823) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=89211823&dopt=Abstract)
Medline (PMID=87065740) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=87065740&dopt=Abstract)
Medline (PMID=93209316) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=93209316&dopt=Abstract)
Medline (PMID=81185784) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=81185784&dopt=Abstract)
Medline (PMID=84179927) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=84179927&dopt=Abstract)
Medline (PMID=82014213) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=82014213&dopt=Abstract)
Medline (PMID=98369748) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=98369748&dopt=Abstract)
Medline (PMID=81122677) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=81122677&dopt=Abstract)
Medline (PMID=80074451) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=80074451&dopt=Abstract)
Medline (PMID=98296296) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=98296296&dopt=Abstract)
Medline (PMID=92277090) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=92277090&dopt=Abstract)
http://www.cpdd.vcu.edu/DEC/acrobat/DEC1997.pdf (http://www.cpdd.vcu.edu/DEC/acrobat/DEC1997.pdf)
would be ineresting for every opiophile.Medline (PMID=91068238) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=91068238&dopt=Abstract)
: Eseroline was comparatively more toxic than the parent compound, physostigmine. You can buy eye-drops, hydrolize physostigmine to eseroline and...kill someone slowly. Search for derivates:Medline (PMID=81122677) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=81122677&dopt=Abstract)
Medline (PMID=92277090) (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=92277090&dopt=Abstract)
http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?rxntypeid=30&prep=CV7P0197 (http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?rxntypeid=30&prep=CV7P0197)
. Do you believe them?