list of phenyltropanes list of phenyltropanes phenyltropanes (pts) are a family of chemical compounds originally derived from structural modification of cocaine. the main feature differentiating phenyltropanes from cocaine is that they lack the ester functionality at the 3-position terminating in the benzene; and thusly the phenyl is attached direct to the tropane skeleton with no further spacer (therefore the name "phenyl"-tropane) that the cocaine benzoyloxy provided. the original purpose of which was to extirpate the cardiotoxicity inherent in the local anesthetic "numbing" capability of cocaine (since the methylated benzoate ester is essential to cocaine's blockage of sodium channels which cause topical anesthesia) while retaining stimulant function. these compounds present many different avenues of research into therapeutic applications, particularly in addiction treatment. uses vary depending on their construction and structure-activity relationship ranging from the treating of cocaine dependency to understanding the dopamine reward system in the human brain to treating alzheimer's & parkinson's diseases. (since 2008 there have been continual additions to the list and enumerations of the plethora of types of chemicals that fall into the category of this substance profile.) certain phenyltropanes can even be used as a smoking cessation aid (c.f. rti-29). many of the compounds were first elucidated in published material by the research triangle institute and are thus named with "rti" serial-numbers (in this case the long form is either rti-coc-n, for 'cocaine' "analog", or specifically rti-4229-n of the subsequent numbers given below in this article) similarly, a number of others are named for sterling-winthrop pharmaceuticals ("win" serial-numbers) and wake forest university ("wf" serial-numbers). the following includes many of the phenyltropane class of drugs that have been made and studied. 3d rendering of troparil; which comprises a privileged scaffold of among the phenyltropane class of compounds. troparil structure: c.f. u.s. patent 5,496,953 2-carboxymethyl esters (phenyl-methylecgonines) epibatropane containing a nitrogen heteroatom in the benzene ring formation. tamagnan: ssri, sert = 17(pm) = 10 times the strength of paroxetine for 5ht. rti-298 (4′-)para-cis-propenyl-phenyl-methylecgonine. a rare sdri compound with negligible net affinity (>2,800.0nm displacement value for net ligand) that retains significant dat & sert (15.0nm & 7.1nm) affinity.c2-c3 unsaturated (non-isomeric, neither α nor β orientated) 2-naphthyl-tropane1-naphthyl-tropane in its usual (comparably non-standard) boat formation of its tropane ring. like cocaine, phenyltropanes are considered a 'typical' or 'classical' (i.e. "cocaine-like") dat re-uptake pump ligands in that they stabilize an "open-to-out" conformation on the dopamine transporter; despite the extreme similarity to phenyltropanes, benztropine and others are in suchwise not considered "cocaine-like" and are instead considered atypical inhibitors insofar as they stabilize what is considered a more inward-facing (closed-to-out) conformational state. considering the differences between pts and cocaine: the difference in the length of the benzoyloxy and the phenyl linkage contrasted between cocaine and phenyltropanes makes for a shorter distance between the centroid of the aromatic benzene and the bridge nitrogen of the tropane in the latter pts. this distance being on a scale of 5.6 å for phenyltropanes and 7.7 å for cocaine or analogs with the benzoyloxy intact. the manner in which this sets phenyltropanes into the binding pocket at mat is postulated as one possible explanation to account for pts increased behavioral stimulation profile over cocaine. blank spacings within tables for omitted data use "no data", "?", "-" or "—" interchangeably. 2β-carbmethoxy-3β-(4′-substituted phenyl)tropanes (ic50 values)monohalogen halide-phenyltropanes (11a—11e) alkyl-, & alkenyl-phenyltropanes (11r—11x) alkynyl-phenyltropanes (11y & 11z) structure short namei.e. trivial iupac(non-systematic) name(singh's #) r (para-substitution)of benzene dawin 35428ic50 nm(ki nm) 5htparoxetineic50 nm(ki nm) nenisoxetineic50 nm(ki nm) selectivity5-htt/dat selectivitynet/dat cocaine(benzoyloxytropane)h102 ± 12241 ± 18ɑ1045 ± 89112 ± 2b3298 ± 293160 ± 15c10.20.5d32.30.7e (para-hydrogen)phenyltropanewin 35,065-2 (β-cpt) troparil11ah23 ± 5.049.8 ± 2.2ɑ1962 ± 61173 ± 13b920 ± 7337.2 ± 5.2c85.33.5d40.00.7e para-fluorophenyltropanewin 35,428 (β-cft)11bf14 (15.7 ± 1.4)22.9 ± 0.4ɑ156 (810 ± 59)100 ± 13b85 (835 ± 45)38.6 ± 9.9c51.64.4d53.21.7e para-nitrophenyltropane11kno210.1 ± 0.10???? para-aminophenyltropanerti-2911jnh29.824.8 ± 1.3g5110151521.415.4 para-chlorophenyltropanerti-3111ccl1.12 ± 0.063.68 ± 0.09ɑ44.5 ± 1.35.00 ± 0.05b37 ± 2.15.86 ± 0.67c39.71.3d33.01.7e para-methylphenyltropanerti-32 tolpane11fme1.71 ± 0.307.02 ± 0.30ɑ240 ± 2719.38 ± 0.65b60 ± 0.53e8.42 ± 1.53c1402.8d35.11.2e para-bromophenyltropanerti-51 bromopane11dbr1.81 (1.69) ± 0.3010.6 ± 0.2437.4 ± 5.25.820.7 para-iodophenyltropanerti-55 (β-cit) iometopane11ei1.26 ± 0.041.96 ± 0.09ɑ4.21 ± 0.31.74 ± 0.23b36 ± 2.77.51 ± 0.82c3.30.9d28.63.8e para-hydroxyphenyltropane11hoh12.1 ± 0.86———— para-methoxyphenyltropane11ioch38.14 ± 1.3———— para-azidophenyltropane11ln32.12 ± 0.13———— para-trifluoromethylphenyltropane11mcf313.1 ± 2.2———— para-acetylaminophenyltropane11nnhcoch364.2 ± 2.6———— para-propionylaminophenyltropane11onhcoc2h5121 ± 2.7———— para-ethoxycarbonylaminophenyltropane11pnhco2c3h5316 ± 48———— para-trimethylstannylphenyltropane11qsn(ch3)3144 ± 37———— para-ethylphenyltropanerti-8311get55 ± 2.128.4 ± 3.8(2.58 ± 3.5)4030 (3910) ± 381(2360 ± 230)0.573.3 para-n-propylphenyltropanerti-282i11rn-c3h768.5 ± 7.170.4 ± 4.13920 ± 1301.057.2 para-isopropylphenyltropane11sch(ch3)2597 ± 52191 ± 9.575000 ± 58200.3126 para-vinylphenyltropanerti-35911tch-ch21.24 ± 0.29.5 ± 0.878 ± 4.17.762.9 para-methylethenylphenyltropanerti-283j11uc(=ch2)ch314.4 ± 0.33.13 ± 0.161330 ± 3330.292.4 para-trans-propenylphenyltropanerti-296i11vtrans-ch=chch35.29 ± 0.5311.4 ± 0.281590 ± 932.1300 para-allylphenyltropane11xch2ch=ch232.8 ± 3.128.4 ± 2.42480 ± 2290.975.6 para-ethynylphenyltropanerti-36011yc≡ch1.2 ± 0.14.4 ± 0.483.2 ± 2.83.769.3 para-propynylphenyltropanerti-281i11zc≡cch32.37 ± 0.215.7 ± 1.5820 ± 466.6346 para-cis-propenylphenyltropanerti-30411wcis-ch=chch315 ± 1.27.1 ± 0.712,800k ± 3000.5186.6k para-(z)-phenylethenylphenyltropanecis-ch=chph11.7 ± 1.12———— para-benzylphenyltropane-ch2-ph526 ± 657,240 ± 390(658 ± 35)6670 ± 377(606 ± 277)13.712.6 para-phenylethenylphenyltropanech2 ║-c-ph474 ± 1332,710 ± 800(246 ± 73)7,060 ± 1,760(4,260 ± 1,060)5.714.8 para-phenylethylphenyltropanel-(ch2)2-ph5.14 ± 0.63234 ± 26(21.3 ± 2.4)10.8 ± 0.3(6.50 ± 0.20)45.52.1 para-(e)-phenylethenylphenyltropanelrti-436trans–ch=chph3.09 ± 0.75335 ± 150(30.5 ± 13.6)1960 ± 383(1180 ± 231)108.4634.3 para-phenylpropylphenyltropanel-(ch2)3-ph351 ± 521,243 ± 381(113 ± 35)14,200 ± 1,800(8,500 ± 1,100)3.540.4 para-phenylpropenylphenyltropanel-ch=ch-ch2-ph15.8 ± 1.31781 ± 258(71 ± 24)1,250 ± 100(759 ± 60)49.479.1 para-phenylbutylphenyltropanel-(ch2)4-ph228 ± 214,824 ± 170(439 ± 16)2,310 ± 293(1,390 ± 177)21.110.1 para-phenylethynylphenyltropanelrti-298–≡–ph3.7 ± 0.1646.8 ± 5.8(4.3 ± 0.53)347 ± 25(209 ± 15)12.693.7 para-phenylpropynylphenyltropanel–c≡c-ch2ph1.82 ± 0.4213.1 ± 1.7(1.19 ± 0.42)27.4 ± 2.6(16.5 ± 1.6)7.115 para-phenylbutynylphenyltropanelrti-430–c≡c(ch2)2ph6.28 ± 1.252180 ± 345(198 ± 31)1470 ± 109(885 ± 66)347.1234 para-phenylpentynylphenyltropanel–c≡c-(ch2)3-ph300 ± 371,340 ± 232(122 ± 21)4,450 ± 637(2,680 ± 384)4.4614.8 para-trimethylsilylethynylphenyltropane—————— para-hydroxypropynylphenyltropane—————— para-hydroxyhexynylphenyltropanel–c≡c-(ch2)4oh57 ± 4828 ± 29(75 ± 2.6)9,500 ± 812(5,720 ± 489)14.5166.6 para-(thiophen-3-yl)phenyltropanetamagnanp-thiophene120.0171890.00141615.7 para-biphenyltropane11aaph10.3 ± 2.6f29.4 ± 3.8ɑ15.6 ± 0.695.8 ± 36(8.7 ± 3.3)1,480 ± 269(892 ± 162)6.194.8 3β-2-naphthyltropanerti-31811bb3β-2-naphthyl0.51 ± 0.033.32 ± 0.08f3.53 ± 0.09ɑ0.80 ± 0.06(0.07 ± 0.1)21.1 ± 1.0(12.7 ± 0.60)1.541.3 para-bimethoxyphenyltropane15och2och3h————— ɑda uptake displacement ki value. b5-ht uptake displacement ki value. cne uptake displacement ki value. d5-ht uptake to da uptake ratio. ene uptake to da uptake ratio. fic50 for displacement of cocaine. gvalues from alternate data-set differing from that used in rest of table. horiginal source (scheme 4, page 931, 7th of article) name given for compound (bottom of first ¶) is at variance with formula in scheme on same page: i.e. "methoxymethyl" versus "methoxymethoxy" iprotonated as the (-)—tartrate salt (isomer) jprotonated as the tartrate salt kwas cited by s. singh as 28,000nm for sert or a dat/sert ratio of 1,867. however, in singh's paper he cited j. med. chem. 1996, 39, 4030, table 1 which shows a ten times lower value, which is consistent with numerous rti patents published showing the ten-× lower value. lwhereas many bulky additions to the arene unit of phenyltropanes hinder and impair affinity, it has been observed that the para-substituted rigid triple bond analogs terminating in a second phenyl (off of the initial c3 position phenyl) have a high-binding affinity, putatively attesting to the existence of another binding domain that extends beyond the usual ending point where the benzene accords to the acceptor somewhere along the length of range inhabited by the dat, corresponding to a 180° extension outward from the para area of the aryl of these type of ligands. (4′-monosubstituted 2,3-thiophene phenyl)-tropanes tamagnan (thiophene) analogues of para-phenyltropanes. compound structure alphanumeric code(name) para-substitution n8 sert dat net selectivitysert versus dat selectivitysert versus net 1(cocaine)(—)-cocainech310508933200.083.2 2(β-cit), (iometopane)iodoch30.46 ± 0.060.96 ± 0.152.80 ± 0.402.16.1 (r,s-citalopram)——1.6016,5406,19010,3383,869 4a2-thiophenech30.15 ± 0.01552 ± 12.8158 ± 123461,053 4b(tamagnan)3-thiophenech30.017 ± 0.00412.1 ± 3189 ± 8271011,118 4c2-(5-br)-thiophenech30.38 ± 0.0086.43 ± 0.9324 ± 1917853 4d2-(5-cl)-thiophenech30.64 ± 0.044.42 ± 1.64311 ± 256.9486 4e2-(5-i)-thiophenech34.56 ± 0.8422.1 ± 3.21,137 ± 1234.9249 4f2-(5-nh2)-thiophenech364.7 ± 3.7>10,000>30,000>155>464 4g2-(4,5-no2)-thiophenech35,000>30,000>10,000>6.0>2.0 4h3-(4-br)-thiophenech34.02 ± 0.34183 ± 69>10,00046>2,488 5a2-thiopheneh0.11 ± 0.00612.2 ± 0.975.3 ± 9.6111685 5b3-thiopheneh0.23 ± 0.026.4 ± 0.2739 ± 0.828170 (3′,4′-disubstituted phenyl)-tropanes compound(+ s. singh's name)x(4′-para)y(3′-meta)2 positionconfig8da5-htne rti-31811bbβ-naphthylco2meβ,βnme0.50.8120 dichloropane (rti-111ɑ)17cclclco2meβ,βnme0.793.1318.0 rti-88 17enh2ico2meβ,βnme1.351329c320c rti-9717dnh2brco2meβ,βnme3.91181282 rti-112b17bclmeco2meβ,βnme0.8210.536.2 rti-9617afmeco2meβ,βnme2.9576520 rti-295etico2meβ,βnme21.32.961349 rti-353 (eint)etico2meβ,βnh3310.69148 rti-279meico2meβ,βnh5.981.0674.3 rti-280meico2meβ,βnme3.126.81484 meltzercatecholco2meβ,βnme>100?? meltzeroacoacco2meβ,βnme??? ɑas ·hcl (salt) bas ·hcl·2 h2o (salt) csingh gives the reverse value with respect to i.e. 1,329 for net & 320 for 5-ht para-meta-substituted 2β-carbomethoxy-3α-(4′-substituted phenyl)tropanes compound short name(s. singh) r2 r1 da 5ht ne selectivity5-htt/dat selectivitynet/dat meta-fluorophenyltropane16afh23 ± 7.8---- meta-chlorophenyltropane16bclh10.6 ± 1.8---- meta-bromophenyltropane16cbrh7.93 ± 0.08ɑ---- meta-iodophenyltropane16dih26.1 ± 1.7---- meta-tributylstannylphenyltropane16esnbu3h1100 ± 170---- meta-ethynylphenyltropanec≡chh----- meta-methyl-para-fluorophenyltropanerti-9617ach3f2.95 ± 0.58---- meta-methyl-para-chlorophenyltropanerti-112c17bch3cl0.81 ± 0.0510.5 ± 0.0536.2 ± 1.013.044.7 meta-para-dichlorophenyltropanerti-111b dichloropane17cclcl0.79 ± 0.08b3.13 ± 0.36b18.0 ± 0.817.96 ± 0.85'b'd4.0b22.8b meta-bromo-para-aminophenyltropanerti-9717dbrnh23.91 ± 0.5918128246.272.1 meta-iodo-para-aminophenyltropanerti-8817einh21.35 ± 0.11120 ± 41329 ± 12488.9984 meta-iodo-para-azidophenyltropane17fin34.93 ± 0.32---- ɑic50 determined in cynomolgous monkey caudate-putamen bas ·hcl (salt) cas ·hcl·2 h2o (salt) dnen 3β-(4-alkylthio, -methylsulfinyl, and -methylsulfonylphenyl)tropanes structure compound r x n inhibition of win 35,428@ datic50 (nm) inhibition of paroxetine@ 5-httki (nm) inhibition of nisoxetine@ netki (nm) net/dat(uptake ratio) net/5-htt(uptake ratio) cocainedes-thio/sulfinyl/sulfonylhhdesmethyl089.19519902221 para-methoxyphenyltropanesingh: 11ides-thio/sulfinyl/sulfonyloch3h06.5 ± 1.34.3 ± 0.51110 ± 64171258 7ach3h09 ± 30.7 ± 0.2220 ± 1024314 7bc2h5h0232 ± 344.5 ± 0.51170 ± 3005260 7cch(ch3)2h016 ± 223 ± 2129 ± 287 7dcf3h0200 ± 708 ± 21900 ± 30010238 7ech3br010.1 ± 10.6 ± 0.2121 ± 1212202 7fch3br176 ± 183.2 ± 0.4690 ± 809216 7gch3h191 ± 164.3 ± 0.6515 ± 606120 7hch3h2>10,000208 ± 45>10,000148 (2′,4′-disubstituted phenyl)-tropanes ortho-para-substituted (2′,4′-disubstituted phenyltropanes) compound structure trivial iupac(non-systematic)name r2ortho r1para da 5ht ne selectivity5-htt/dat selectivitynet/dat ortho,para-dinitrophenyltropaneno2no2----- (3′,4′,5′-trisubstituted para-methoxyphenyl)-tropanes para-meta(3′)-meta(5′)-(di-meta)-substituted 2β-carbomethoxy-(3′,4′,5′-substituted phenyl)tropanespara-methoxy/(ethoxy)-meta-substituted phenyltropanes structure short name(all compounds tested as hcl salts) r23′-(meta) r35′-(di-meta) or14′-(para) datic50(compound #)12 5-httkiparoxetine netkinisoxetine selectivitynet/datratioki/ic50 selectivitynet/5-httratioki/ki cocaine---89.19519902221 6rti-112---0.82 ± 0.050.95 ± 0.0421.8 ± 0.62723 7a11ihhch36.5 ± 1.34.3 ± 0.51110 ± 64171258 7bhhc2h592 ± 81.7 ± 0.41690 ± 5018994 7cfhch316 ± 14.8 ± 0.5270 ± 501756 7dbrhch347 ± 153.1 ± 0.1160 ± 20352 7fbrbrch392 ± 222.9 ± 0.14100 ± 400ɑ451413 7eihch3170 ± 603.5 ± 0.4180 ± 20151 7giich31300 ± 2007.5 ± 0.8180 ± 204667 ɑn=2 (2′,4′,5′-trisubstituted phenyl)-tropanes ortho-para(4′)-meta(5′)-trisubstituted 2β-carbomethoxy-(2′,4′,5′-substituted phenyl)tropanes structure short name r12′-(ortho) r24′-(para) r35′-(meta) dat 5-htt net selectivitynet/datratio selectivitynet/5-httratio para-ethyl-ortho, meta-diiodophenyltropaneiodoethyliodo----- 2-carbmethoxy modified (replaced/substituted) 2β-substitutions of p-methoxy-phenyltropanes para-och3-(3β-(4-methoxyphenyl)tropane-2β-carboxylic acid ester analogues structure short name(all compounds tested as hcl salts) co2r (2β-substituted)(compound 9 is 2β=r) datic50(compound #)12 5-httkiparoxetine netkinisoxetine selectivitynet/datratioki/ic50 selectivitynet/5-httratioki/ki 7a11ich36.5 ± 1.34.3 ± 0.51110 ± 64171258 8a(ch3)2ch14 ± 3135 ± 352010 ± 20014415 8bcyclopropane6.0 ± 229 ± 31230 ± 14020542 8ccyclobutane13 ± 3100 ± 8>300023130 8do2n...1,4-xylene...(ch2)242 ± 82.9 ± 0.2330 ± 208114 8eh2n...1,4-xylene...(ch2)27.0 ± 28.3 ± 0.42200 ± 300ɑ314265 8fch3conh...1,4-xylene...(ch2)26.0 ± 15.5 ± 0.51460 ± 30243265 8gh2n...2-bromo-1,4-dimethylbenzene...(ch2)23.3 ± 1.44.1 ± 0.61850 ± 90561451 8hh2n...1,3-dibromo-2,5-dimethylbenzene...(ch2)215 ± 62.0 ± 0.42710 ± 250ɑ1811360 8ih2n...2-iodo-1,4-dimethylbenzene...(ch2)22.5 ± 0.73.5 ± 12040 ± 300ɑ816583 8jh2n...1,3-diiodo-2,5-dimethylbenzene...(ch2)2102 ± 151.0 ± 0.12600 ± 200ɑ252600 93-(4-methylphenyl)-1,2-oxazole18 ± 6860 ± 170>30001673 ɑn=2 2β-carboxy side-chained (p-chloro/iodo/methyl) phenyltropanes multi-substituted structures of 2β-ester-3β-phenyltropanes compound short name(s. singh) r x ic50 (nm)datwin 35428 ic50 (nm)5-httparoxetine ic50 (nm)netnisoxetine selectivity5-htt/dat selectivitynet/dat 23ach(ch3)2h85.1 ± 2.523121 ± 397632047 ± 1491272376 23bc6h5h76.7 ± 3.6106149 ± 725619262 ± 5931384251 24ach(ch3)2cl1.4 ± 0.136.04 ± 0.31ɑ1400 ± 7128 ± 15b778 ± 21250 ± 0.9c100021.2d55641.4e 24bcyclopropylcl0.96 ± 0.10168 ± 1.8235 ± 8.39175245 24cc6h5cl1.99 ± 0.055.25 ± 0.76ɑ2340 ± 27390 ± 34b2960 ± 220242 ± 30c117674.3d1.341.6e 24dc6h4-4-icl32.6 ± 3.91227 ± 176967.6 ± 26.337.629.7 24ec6h4-3-ch3cl9.37 ± 0.522153 ± 1432744 ± 140230293 24fc6h4-4-ch3cl27.4 ± 1.51203 ± 421277 ± 11843.946.6 24gc6h4-2-ch3cl3.91 ± 0.233772 ± 3844783 ± 3879651223 24hc6h4-4-clcl55 ± 2.316914 ± 10564883 ± 28830788.8 24ic6h4-4-och3cl71 ± 5.619689 ± 18431522 ± 9427721.4 24j(ch2)2c6h4-4-no2cl2.71 ± 0.13---- 24k(ch)2c6h4-4-nh2cl2.16 ± 0.25---- 24l(ch2)2c6h3-3-i-4-nh2cl2.51 ± 0.25---- 24m(ch2)2c6h3-3-i-4-n3cl14.5 ± 0.94---- 24n(ch2)2c6h4-4-n3cl6.17 ± 0.57---- 24o(ch2)2c6h4-4-ncscl5.3 ± 0.6---- 24p(ch2)2c6h4-4-nhcoch2brcl1.73 ± 0.06---- 25ach(ch3)2i0.43 ± 0.052.79 ± 0.13ɑ66.8 ± 6.5312.5 ± 1.0b285 ± 7.641.2 ± 3.0c1554.5d66314.8e 25bcyclopropyli0.61 ± 0.0815.5 ± 0.72102 ± 1125.4167 25cc6h5i1.51 ± 0.346.85 ± 0.93ɑ184 ± 2251.6 ± 6.2b3791 ± 14932.7 ± 4.4c1227.5d25104.8e 26ach(ch3)2ch36.45 ± 0.8515.3 ± 2.08ɑ6090 ± 488917 ± 54b1926 ± 3873.4 ± 11.6c94459.9d2994.8e 26bch(c2h5)2ch319.1 ± 14499 ± 5573444 ± 44235180 26ccyclopropylch317.8 ± 0.76485 ± 212628 ± 25227.2148 26dcyclobutylch33.74 ± 0.522019 ± 1334738 ± 3225401267 26ecyclopentylch31.68 ± 0.141066 ± 109644 ± 28634383 26fc6h5ch33.27 ± 0.069.13 ± 0.79ɑ24500 ± 15261537 ± 101b5830 ± 370277 ± 23c7492168d178330.3e 26gc6h4-3-ch3ch38.19 ± 0.905237 ± 4532136 ± 208639261 26hc6h4-4-ch3ch381.2 ± 1615954 ± 6144096 ± 12119650.4 26ic6h4-2-ch3ch323.2 ± 0.9711040 ± 50425695 ± 13944761107 26jc6h4-4-clch3117 ± 7.942761 ± 23999519 ± 86436581.3 26kc6h4-4-och3ch395.6 ± 8.882316 ± 78523151 ± 28286133.0 ɑki value for displacement of da uptake. bki value for displacement of 5-ht uptake. cki value for displacement of ne uptake. d5-ht uptake to da uptake ratio. ene uptake to da uptake ratio. carboxyaryl compoundx2 positionconfig8da5-htne rti-122i-co2phβ,βnme1.501843,791 rti-113cl-co2phβ,βnme1.982,3362,955 rti-277no2-co2phβ,βnme5.942,9105,695 rti-120 me-co2phβ,βnme3.2624,4715,833 rti-116cl-co2(p-c6h4i)β,βnme331,227968 rti-203clco2(m-c6h4me)β,βnme9.3721532744 rti-204cl-co2(o-c6h4me)β,βnme3.913,7724,783 rti-205me-co2(m-c6h4me)β,βnme8.195,2372,137 rti-206cl-co2(p-c6h4me)β,βnme27.41,2031,278 2-phenyl-3-phenyltropanes 2-phenyl-3-phenyltropane binding affinities and inhibition of da & 5-ht uptake compound structure short name(s. singh) stereochemistry x(para) datwin 35428 ic50 (nm) datmazindol ki (nm) 5-httparoxetine ic50 (nm) da uptake ki (nm) 5-ht uptake ki (nm) selectivity5-ht/da cocaine(2β,3β)(h)89 ± 4.82811050 ±