v. Braun, Julius et al. published their research in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1927 | CAS: 207451-81-8

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) belongs to tetrahydroisoquinoline derivatives. There has been increasing research interest and speculation since 1968 in the potential formation of tetrahydroisoquinoline (TIQ) alkaloids in mammalian cells via such interactions, and in the role such TIQs may have in alcohol dependence. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This is no longer generally accepted by the scientific community.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

Synthesis of tetrahydroisoquinoline and as-homotetrahydroisoquinoline bases by the glycine-aluminum chloride method. II was written by v. Braun, Julius;Wirz, Karl. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1927.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

Just as Ph(CH2)nN(SO2Ph)CH2COCl with AlCl3 loses CO2 and forms C6H4.(CH2)n.N(SO2Ph).CH2, when n = 2 or 3, so Ph(CH2)2NMeCH2COCl (I) has now been found to yield N-methyltetrahydroisoquino-line (II) smoothly. The new “glycine-AlCl3 method” of synthesizing tetrahydro- and as-homotetrahydroisoquinoline has been successfully applied to the synthesis of various derivatives of these compounds Et β-phenylethymethylglycine, Ph(CH2)2NMeCH2CO2Et, from PhCH2CH2NHMe in Et2O with 0.5 mol. BrCH2CO2Et, b12 151 5°; methiodide, m. 160°. Frec acid, m. 163°, obtained as the HCl salt, m. 155°, by evaporating the ester with HCl; the acid with PCl5 and cold AcCl gives the HCl salt of the chloride (I) which decomposes so rapidly in the air that it could not be accurately analyzed; this salt with AlCl3 yields more than 40% of the HCl salt, m. 163°, of II, b. 213° (picrate, m. 146°; methiodide, m. 189°). p-MeC6H4CH2CH2OH, obtained in 80% yield from MeC6H4Br, Mg and ClCH2CH2OH, was converted through the bromide, b14 115°, and the phthalimide, MeC6H4CH2CH2N(CO)2C6H4, m. 113°, into the amine, which with BrCH2CO2Et smoothly yielded the ester p-MeC6H4CH2NHCH2CO2Et, b12 176-7°; this with HCl gave the free glycine-HCl, m. 216°, converted into the benzenesulfonyl derivative, MeC6H4CH2CH2N(SO2Ph)CH2CO2H, which with PCl5 and AlCl3 yielded 65% of the benzenesulfonyl derivative, m. 154°, of 7-methyltetrahydroisoquinoline, b18 125°, d424 1.0176 (HCl salt, m. 216°; picrate, m. 202°; methiodide, m. 133°; NO derivative, m. 87°). β-p-Tolylethyl cyanide, from the bromide and KCN (yield, more than 90%), b15 137°, is reduced by the Ladenburg method to the propylamine, b23 126°, quickly absorbs CO2 from the air (HCl salt, m. 225°; picrate, yellow, m. 154°; Bz derivative, m. 85°; phenylthiourea, m. 82°), gives with BrCH2CO2Et the ester MeC6H4(CH2)3NHCH2CO2Et, b22 191°. Free glycine-HCl, m. 211°; benzenesulfonyl derivative, m. 116°, yields almost 70% of the benzenesulfonyl derivative, m. 126°, of 8-methyl-as-homotetrahydroisoquinoline, b19 137-9° m. 27°, d423 1.0048 (HCl salt, m. 223°; Bz derivative, m. 101°; NO derivative, m. 91°). β-p-Isopropylphenylethyl alc. (60% from p-Me2CHC6H4Br, Mg and ClCH2CH2OH), b20 147°; bromide, b20 134-6°; cyanide, b17 150°; propylamine. b20 143° (HCl salt, m. 196°; picrate, m. 122°; Bz derivative, m. 71°). The ester Me2CHC6H4(CH2)3NHCH2CO2Et, b20 205-10°. Free acid-HCl, m. 210°; benzenesulfonyl derivative, m. 101°, yields 70% of the benzenesulfonyl derivative, m. 92°, of 8-isopropyl-as-homotetrahydroisoquinoline, m. 31° (HCl salt, m. 248°; picrate, m. 236° ; methiodide, m. 214°; Bz derivative, m. 83°; NO derivative, m. 70°). Piperonal (300 g.) can be quant. reduced in less than 1 hr. with H and Ni in decalin at 120-30° to the alc., m. 54°, b18 157°, whose chloride with KCN in aqueous Me2CO at 100° yields with extraordinary smoothness the cyanide, m. 42°, b30 180°, and this with Na and alc. gives 60% of homopiperonylamine; the ester formed from this with BrCH2CO2Et is hydrolyzed with such ease that the product of the reaction is almost exclusively the free glycine-HCl, m. 241°; the benzenesulfonyl derivative, CH2O2C6H3CH2CH2N(SO2Ph)CH2CO2H, m. 131°, yields with PCl5 and AlCl3 only a black semi-solid mass from which no homogeneous product could be isolated. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) belongs to tetrahydroisoquinoline derivatives. There has been increasing research interest and speculation since 1968 in the potential formation of tetrahydroisoquinoline (TIQ) alkaloids in mammalian cells via such interactions, and in the role such TIQs may have in alcohol dependence. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This is no longer generally accepted by the scientific community.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem